化学酶法制备他汀药物关键手性中间体的研究
|
摘要
他汀药物是一类新型,最畅销的降血脂药物。它通过对人体胆固醇合成过程中的限速酶,3-羟基-3-甲基辅酶A(HMG-CoA)还原酶的抑制作用,减少细胞内游离胆固醇生成,最终降低血清中总胆固醇和低密度胆固醇水平。本文重点研究了几个关键手性中间体合成方法和工艺。主要内容包括:
(1)优化了(S)-6-氯-5-羟基-3-羰基己酸叔丁酯和(R)-6-氰基-5-羟基-3-羰基己酸叔丁酯的合成工艺。通过对反应机理分析和各种条件实验,确定了较优的反应条件。改进了(R)-4-氰基-3-羟基丁酸乙酯的合成工艺,确定了以反应溶剂EtOH/H_2O,反应温度35℃,四丁基溴化铵为催化剂的反应体系。该反应工艺生产成本低,反应条件温和,产物纯度和收率高,适合工业化生产。
(2)提出了化学酶法合成(S)-6-苄氧基-5-羟基-3-羰基己酸叔丁酯的新路线。并探讨了在有机相中,脂肪酶催化转酯化拆分4-芳甲氧基-3-羟基-丁腈。以4-苯甲氧基-3-羟基-丁腈做为模板化合物,通过酶和溶剂筛选,选择了脂肪酶Artgribacter sp.,确定了混合溶剂(乙腈/正庚烷=1:1)作为反应体系。并用该方法对不同取代基的4-芳甲氧基-3-羟基-丁腈进行了研究,发现脂肪酶Artgribactersp.对底物的反应选择性,随着芳环上取代基数量的增加而增大。
(3)提出了化学法合成(3R,5S)-6-羟基-3,5-氧-异亚丙基-3,5-二羟基己酸叔丁酯的新路线。采用(R)-环氧氯丙烷为原料,经过几步条件温和的反应合成了目标化合物(3R,5S)-6-羟基-3,5-氧-异亚丙基-3,5-二羟基己酸叔丁酯。在第一步反应中,使用三氟化硼作为催化剂,高光学选择性的引入手性羟基;在制备化合物(S)-3-羟基-4-苄氧基丁腈过程中,比较两条不同的路径,确定了最佳反应途径;(S)-3-羟基-4-苄氧基丁腈经过羟基保护,与溴乙酸叔丁酯缩合,三乙基硼手性诱导还原,经过二羟基保护,最后催化加氢脱去对甲苄基得到目标产物。与以前报道工艺相比,本工艺具有反应条件比较温和,反应试剂便宜、易得等优点。
(4)提出了酶法和化学法拆分制备(3R,5S)-6-羟基-3,5-氧-异亚丙基-3,5-二羟基己酸叔丁酯的新方法。其手性中心C-5通过脂肪酶转酯拆分得到,手性中心C-3通过化学法拆分得到。
在酶法制备手性中心C-5的过程中,探讨了在有机相中脂肪酶催化转酯化拆分1-芳基-3-氯-2-丙醇。以1-苯甲氧基-3-氯-2-丙醇做为模板化合物,通过酶和溶剂的筛选,确定了脂肪酶Alcaligenes sp.为反应用酶,混合溶液(乙腈/正己烷,1:3,v/v)作为反应溶剂。并用该体系对不同取代基的1-芳甲氧基-3-氯-2-丙醇反应进行了研究,确定酶选择性最佳底物1-(4-甲基苯甲氧基)-3-氯-2-丙醇为合成手性C-5的反应底物。
为了得到手性中心C-3,探讨了溶剂对硼氢化钠选择性还原(5S)-6-对甲基苄氧基-5-羟基-3-羰基已酸叔丁酯的影响,在异丙醇水溶液中,产物(5S)-6-对甲基苄氧基-3,5-二羟基已酸叔丁酯中顺式和反氏的比例达到了4.0:1。酸水解拆分(5S)-6-对甲基苄氧基-3,5-氧-异亚丙基-3,5-二羟基己酸叔丁酯高选择性的得到顺式(3R,5S)-6-对甲基苄氧基-3,5-氧-异亚丙基-3,5-二羟基己酸叔丁酯,de值为98%,收率65%。
(5)对(4R-cis)6-氰(氯)基-2,2-二甲基-1,3-二氧六环-4-乙酸叔丁酯的合成工艺进行了优化。以(S)-环氧氯丙烷为原料,经过与NaCN加成,羟基保护,与溴乙酸叔丁酯缩合得到了(S)-6-氯基-5-羟基-3-羰基已酸叔丁酯。(S)-6-氯基-5-羟基-3-羰基已酸叔丁酯经过氰基取代后,经三乙基硼诱导还原,二羟基保护得到(4R-cis)-6-氰基-2,2-二甲基-1,3-二氧六环-4-乙酸叔丁酯。本工艺具有简单,环境友好,生产成本低等优点。
Statin is one of new and best-selling medicines which is used as an inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme-A reductase(HMG-CoA),the rate limiting enzyme in cholesterol biosynthesis.This medicine can reduce the forming of dissociated cholesterol in cells and thus lower plasma an low density lipoprotein cholesterol in blood.In this dissertation,some new synthetic methods and technologies to its key structures are emphatically described.The main contents of this work are as follows:
(1)The synthetic technology for the construction of tert-butyl(S)-6-chloro-5-hydroxyl-3-oxohexanoatewas optimized.Through analysis of reaction mechanism and operation of different experiments,the optimum reaction condition was obtained. Meanwhile,synthetic technology for the synthesis of ethyl(R)-4-cyano-3-hydroxybutanaote was improved,and the good reaction condition was that EtOH/H_2O,35℃and tetrabutylammonium bromide were selected as the reaction solvent,temperature and catalyzer,respectively.The synthetic technology were suitable for industrial production for its low manufacturing cost,mild reaction conditions,high purities and good yields.
(2)A chemoenzymatie synthesis of tert-butyl(S)-6-benzyloxy-5-hydroxy-3-oxo-hexanoate was described.The kinetic resolution of 4-arylmethoxy-3-hydroxybutane-nitriles was investigated by lipase-catalyzed transesterification in organic solvent.High enantioselectivity was obtained by reaction with vinyl acetate in mixed solvent(n-heptane/acetonitrile 1:1),which was catalyzed by the lipase from Artgribacter sp.Better selectivity was demonstrated with the number of substituents on the aryl ring increasing.
(3)A new synthetic method of(4R,6S)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester was accomplished.The target compound was successfully prepared via several mild reaction processes by using R-epichlorohydrin,which is an easily available starting material.Through comparing with three different synthetic methods,the best route was obtained.Dihydroxy ester was synthesized by a syn-selective triethylborane reduction with de value of 97%. After acid-catalyzed protection of dihydroxy ester and hydrogenolysis of the benzyl protecting group,the objective was obtained with high enantiomeric and diastereomeric purity.
(4)A facile route to synthesis tert-butyl(3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate by a chemoenzymatic approach was described.
To get the hydroxyl stereocenter at C5,the kinetic resolution of 1-arylmethoxy -3-chloro-2-propanols was investigated by lipase-catalyzed esterification in organic solvents.High enantioselectivity was obtained by reaction with vinyl acetate in mixed solvent(n-hexane/acetonitrile 3:1),which was catalyzed by the lipase from Alcaligenes sp.1-(4-methylbenzyloxy)-3-chloro-2-propanol was enantioselectively resolved by lipase from Alcaligenes sp.with excellent enantioselectivity(E≥200)and chosen as the optimum subtrate.
Another hydroxyl stereocenter at C3 was built by a three-step method,first sodium borohydride reduction of tert-butyl(S)-6-(4-methybenzyloxy)-5-hydroxy-3-oxohexanoate in aqueous isopropyl alcohol with a high disastereomeric ratio(dr_(s:a)= 4.0:1),then acetonide protection,followed by hydrolysis of tert-butyl (5S)-6-(4-methybenzyloxy)-3,5-O-isopropylidene-3,5-dihydroxyhexanoate with acid solutions.The compound tert-butyl(3R,5S)-6-(4-methybenzyloxy)-3,5-O-isopropylidene-3, 5-dihydroxyhexanoate was obtained in 65%yield and 98.0%de.
(5)A new synthesis method of tert-butyl(4R-cis)-6-cyanoxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate was achieved,which started from(S)-epichiorohydrin, followed by addition with sodium cyanide,hydroxyl-group protection, condensation,substitution,syn-selective reduction and dihydroxyl-group protection. This route was suitable for large-scale preparation for its high yields,mild reaction conditions,easily available materials and facile purification of products.
(1)优化了(S)-6-氯-5-羟基-3-羰基己酸叔丁酯和(R)-6-氰基-5-羟基-3-羰基己酸叔丁酯的合成工艺。通过对反应机理分析和各种条件实验,确定了较优的反应条件。改进了(R)-4-氰基-3-羟基丁酸乙酯的合成工艺,确定了以反应溶剂EtOH/H_2O,反应温度35℃,四丁基溴化铵为催化剂的反应体系。该反应工艺生产成本低,反应条件温和,产物纯度和收率高,适合工业化生产。
(2)提出了化学酶法合成(S)-6-苄氧基-5-羟基-3-羰基己酸叔丁酯的新路线。并探讨了在有机相中,脂肪酶催化转酯化拆分4-芳甲氧基-3-羟基-丁腈。以4-苯甲氧基-3-羟基-丁腈做为模板化合物,通过酶和溶剂筛选,选择了脂肪酶Artgribacter sp.,确定了混合溶剂(乙腈/正庚烷=1:1)作为反应体系。并用该方法对不同取代基的4-芳甲氧基-3-羟基-丁腈进行了研究,发现脂肪酶Artgribactersp.对底物的反应选择性,随着芳环上取代基数量的增加而增大。
(3)提出了化学法合成(3R,5S)-6-羟基-3,5-氧-异亚丙基-3,5-二羟基己酸叔丁酯的新路线。采用(R)-环氧氯丙烷为原料,经过几步条件温和的反应合成了目标化合物(3R,5S)-6-羟基-3,5-氧-异亚丙基-3,5-二羟基己酸叔丁酯。在第一步反应中,使用三氟化硼作为催化剂,高光学选择性的引入手性羟基;在制备化合物(S)-3-羟基-4-苄氧基丁腈过程中,比较两条不同的路径,确定了最佳反应途径;(S)-3-羟基-4-苄氧基丁腈经过羟基保护,与溴乙酸叔丁酯缩合,三乙基硼手性诱导还原,经过二羟基保护,最后催化加氢脱去对甲苄基得到目标产物。与以前报道工艺相比,本工艺具有反应条件比较温和,反应试剂便宜、易得等优点。
(4)提出了酶法和化学法拆分制备(3R,5S)-6-羟基-3,5-氧-异亚丙基-3,5-二羟基己酸叔丁酯的新方法。其手性中心C-5通过脂肪酶转酯拆分得到,手性中心C-3通过化学法拆分得到。
在酶法制备手性中心C-5的过程中,探讨了在有机相中脂肪酶催化转酯化拆分1-芳基-3-氯-2-丙醇。以1-苯甲氧基-3-氯-2-丙醇做为模板化合物,通过酶和溶剂的筛选,确定了脂肪酶Alcaligenes sp.为反应用酶,混合溶液(乙腈/正己烷,1:3,v/v)作为反应溶剂。并用该体系对不同取代基的1-芳甲氧基-3-氯-2-丙醇反应进行了研究,确定酶选择性最佳底物1-(4-甲基苯甲氧基)-3-氯-2-丙醇为合成手性C-5的反应底物。
为了得到手性中心C-3,探讨了溶剂对硼氢化钠选择性还原(5S)-6-对甲基苄氧基-5-羟基-3-羰基已酸叔丁酯的影响,在异丙醇水溶液中,产物(5S)-6-对甲基苄氧基-3,5-二羟基已酸叔丁酯中顺式和反氏的比例达到了4.0:1。酸水解拆分(5S)-6-对甲基苄氧基-3,5-氧-异亚丙基-3,5-二羟基己酸叔丁酯高选择性的得到顺式(3R,5S)-6-对甲基苄氧基-3,5-氧-异亚丙基-3,5-二羟基己酸叔丁酯,de值为98%,收率65%。
(5)对(4R-cis)6-氰(氯)基-2,2-二甲基-1,3-二氧六环-4-乙酸叔丁酯的合成工艺进行了优化。以(S)-环氧氯丙烷为原料,经过与NaCN加成,羟基保护,与溴乙酸叔丁酯缩合得到了(S)-6-氯基-5-羟基-3-羰基已酸叔丁酯。(S)-6-氯基-5-羟基-3-羰基已酸叔丁酯经过氰基取代后,经三乙基硼诱导还原,二羟基保护得到(4R-cis)-6-氰基-2,2-二甲基-1,3-二氧六环-4-乙酸叔丁酯。本工艺具有简单,环境友好,生产成本低等优点。
Statin is one of new and best-selling medicines which is used as an inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme-A reductase(HMG-CoA),the rate limiting enzyme in cholesterol biosynthesis.This medicine can reduce the forming of dissociated cholesterol in cells and thus lower plasma an low density lipoprotein cholesterol in blood.In this dissertation,some new synthetic methods and technologies to its key structures are emphatically described.The main contents of this work are as follows:
(1)The synthetic technology for the construction of tert-butyl(S)-6-chloro-5-hydroxyl-3-oxohexanoatewas optimized.Through analysis of reaction mechanism and operation of different experiments,the optimum reaction condition was obtained. Meanwhile,synthetic technology for the synthesis of ethyl(R)-4-cyano-3-hydroxybutanaote was improved,and the good reaction condition was that EtOH/H_2O,35℃and tetrabutylammonium bromide were selected as the reaction solvent,temperature and catalyzer,respectively.The synthetic technology were suitable for industrial production for its low manufacturing cost,mild reaction conditions,high purities and good yields.
(2)A chemoenzymatie synthesis of tert-butyl(S)-6-benzyloxy-5-hydroxy-3-oxo-hexanoate was described.The kinetic resolution of 4-arylmethoxy-3-hydroxybutane-nitriles was investigated by lipase-catalyzed transesterification in organic solvent.High enantioselectivity was obtained by reaction with vinyl acetate in mixed solvent(n-heptane/acetonitrile 1:1),which was catalyzed by the lipase from Artgribacter sp.Better selectivity was demonstrated with the number of substituents on the aryl ring increasing.
(3)A new synthetic method of(4R,6S)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester was accomplished.The target compound was successfully prepared via several mild reaction processes by using R-epichlorohydrin,which is an easily available starting material.Through comparing with three different synthetic methods,the best route was obtained.Dihydroxy ester was synthesized by a syn-selective triethylborane reduction with de value of 97%. After acid-catalyzed protection of dihydroxy ester and hydrogenolysis of the benzyl protecting group,the objective was obtained with high enantiomeric and diastereomeric purity.
(4)A facile route to synthesis tert-butyl(3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate by a chemoenzymatic approach was described.
To get the hydroxyl stereocenter at C5,the kinetic resolution of 1-arylmethoxy -3-chloro-2-propanols was investigated by lipase-catalyzed esterification in organic solvents.High enantioselectivity was obtained by reaction with vinyl acetate in mixed solvent(n-hexane/acetonitrile 3:1),which was catalyzed by the lipase from Alcaligenes sp.1-(4-methylbenzyloxy)-3-chloro-2-propanol was enantioselectively resolved by lipase from Alcaligenes sp.with excellent enantioselectivity(E≥200)and chosen as the optimum subtrate.
Another hydroxyl stereocenter at C3 was built by a three-step method,first sodium borohydride reduction of tert-butyl(S)-6-(4-methybenzyloxy)-5-hydroxy-3-oxohexanoate in aqueous isopropyl alcohol with a high disastereomeric ratio(dr_(s:a)= 4.0:1),then acetonide protection,followed by hydrolysis of tert-butyl (5S)-6-(4-methybenzyloxy)-3,5-O-isopropylidene-3,5-dihydroxyhexanoate with acid solutions.The compound tert-butyl(3R,5S)-6-(4-methybenzyloxy)-3,5-O-isopropylidene-3, 5-dihydroxyhexanoate was obtained in 65%yield and 98.0%de.
(5)A new synthesis method of tert-butyl(4R-cis)-6-cyanoxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate was achieved,which started from(S)-epichiorohydrin, followed by addition with sodium cyanide,hydroxyl-group protection, condensation,substitution,syn-selective reduction and dihydroxyl-group protection. This route was suitable for large-scale preparation for its high yields,mild reaction conditions,easily available materials and facile purification of products.
引文
1.降脂药物市场前景乐观.中国医药报,2006-4-21,第1版.
2.鄢华,高炜,他汀类药物作用和作用机制的新认识.临床内科杂志,2006,23(1):5-7.
3.Executive Summary of the Third Report of the National Cholesterol Education Program (NCEP)Expert Panel on Detection,Evaluation,and Treatment of High Blood Cholesterol in Adults(Adult Treatment Panel Ⅲ).JAMA,2001,285:2486-2497.
4.梁丽,采用他汀类药物进行更积极的降脂治疗.中国医学论坛 2001-10-18,第5版.
5.Endo A,Monacolin k,A new hypocholesterolemic agent produced by a monascus species.J Antibiot,1979,32(8):852-854.
6.Alberts AW,Chen J,Kuron G,Hunt V,Huff J,Hoffman C,Rothrock J,Lopez M,Joshua H,Harris E,Patchett A,Monaghan R,Curfie S,Stapley E,Albers-Schonherg G,Hensens O,Hirshfield J,Hoogsteen K,Liesch J,Springer J,Mevinolin:A highly potent competitive inhibitor of hydroxymethylglutaryl coenzyme-a reductase and a cholesterol lowering agent.Proc.Nati.Acad.Sci.,1980,77(12):3957-3961.
7.Hoffman WF,Albers AW,Anderson PS,Chen JS,Smith RL,Willard AK,3-Hydroxy-3-methylglutaryl-coenzyme A Reductase Inhibitors.4.Side Chain Esters Derivatives of Mevinolin.J.Med.Chem.,1986,29:849-852.
8.Serizawa N,Nakagawa K,Hanano K,Microbial hydroxylation of ML-236B(compaction)and monacolin K(MB-530B).J Antibiot.,1983,36(5):604-607.
9.Tarr L,Pravastatin:A "new" advance in lipid therapy,Scrip 1988,1356:22-23.
10.贺爱珍,胡迎富,丁娟,魏立新,氟伐他汀钠降脂疗效的临床观察.临床心血管病杂志,2001,17(1):37.
11.Baumann KL,Butler DE,Deering CF,Mermen KE,Miilar A,Nanninga TN,Palmer CW,Roth BD,The convergent synthesis of CI-981,an optically active,highly potent,tissue selective inhibitor of HMG-CoA reductase.Tetrahedron Letters,1992,33(17):2283-2284.
12.Quirk J,Thornton M,Kirkpatdck P,Rosuvastatin calcium.News & Analysis,2003,2:769-770.
13.何笑荣,邹定,姜文清,马捷,李金娥,降血脂新药匹伐他汀.中国新药杂志,2005,14(4):483-487.
14.Suzuki M,Iwasaki H,Fujikawa Y,Kitahara M,Sakashita M,Sakoda R,Synthesis and biological evaluations of quinoline-based HMG-CoA reductase inhibitors.Bioorganic &Medicinal Chemistry,2001,9(10):2727-2743.
15.杨亚莉,降血脂新药-西立伐他汀从市场撤出.中国药事,2001,5(15):342.
16.Bischoff H,Angerbauer R,Berder J,Cerivastatin:pharmacology of a novel synthetic and highly active HMG-CoA reductase inhibitor.Atherosclerosis,1997,135:119-130.
17.黄震华,新型调脂药物西立伐他汀.中国新药与临床杂志,2000,19(5):345-347.
18.Endo A,Kuroda M,Tsujita Y,ML-236A,ML-236B and ML-236C,New inhibitors of cholesterogenesis produced by penicillium citrinum,J Antibiot 1976,29(12):1346-1348.
19.Wattanasin S,Do HD,Bhongle N,Kathawala FG,Enantiomerie synthesis of the.beta.-lactone precursor of the HMG-CoA synthase inhibitor(+)-F-(244).J.Chem.Org.1993,58:1610-1612.
20.Stokker GE,Synthesis of L-669,262,a Potent HMG-CoA Reductase Inhibitor.J.Chem.Org.1994,59:5983-5986.
21.Inoue M,Nakada M,Structure Elucidation and Enantioselective Total Synthesis of the Potent HMG-CoA Reductase Inhibitor FR901512 via Catalytic Asymmetric Nozaki-Hiyama Reactions.J.Am.Chem.Soc.2007,129(14):4164-4165.
22.Konoike T,Okada T,Araki Y,Optical Resolution of 3-(Silyloxy)glutaric Acid Half Esters and Their Utilization for Enantioconvergent Synthesis of a HMG-CoA Reductase Inhibitor.J.Org.Chem.1998,63(9):3037-3040.
23.Wess G,Kramer W,Han XB,Bock K,Enhsen A,Glombik H,Baringhaus K-H,Boeger G,Urmann M,et al.,Synthesis and Biological Activity of Bile Acid-Derived HMG-CoA Reductase Inhibitors.The Role of 21-Methyl in Recognition of HMG-CoA Reduetase and the Ileal Bile Acid Transport System.J.Med.Chem.1994,37(20):3240-3246.
24.Zhang QY,Wan J,Xu X,Yang GF,Ren YL,Liu JJ,Wang H,Guo Y,Structure-Based Rational Quest for Potential Novel Inhibitors of Human HMG-CoA Reduetase by Combining CoMFA 3D QSAR Modeling and Virtual Screening.J.Comb.Chem.2007,9(1):131-138.
25.Istvan ES,Deisenhofer J,Structural Mechanism for Statin Inhibition of HMG-CoA Reduetase.Science,2001,292:1160-1164.
26.傅志君,尤启冬,唐伟方,李志裕,他汀类药物作用模式和构效关系研究进展.中国 药学杂志,2003,38(6):404-407.
27.蔡正艳,宁奇,周伟澄,HMG-CoA还原酶抑制剂的合成(上).中国医药工业杂志,2004,35(10):621-626.
28.蔡正艳,宁奇,周伟澄,HMG-CoA还原酶抑制剂的合成(下).中国医药工业杂志,2004,35(11):687-691.
29.陈碧珊,苏丽华,他汀类药物的研究进展.中国药房,2005,16(7):545-546.
30.蔡正艳,宁奇,周伟澄,氟伐他汀钠的合成.中国医药工业杂志,2007,38(2):73-75.
31.蔡伟,张国英,赵文镜,罗永慧,瑞舒伐他汀钙的合成.江苏药学与临床研究,2005,13(4):9-10.
32.Konoike T,Araki Y,Practical Synthesis of Chiral Synthons for the Preparation of HMG-CoA Reductase Inhibitors.J.Org.Chem.1994,59(25):7849-7854.
33.Wess G,Kesseler K,Baader E,Bartmann W,Beck G,Bergmann A,Jendralla H,Bock K,Holzstein O,Kleine H,Schnierer M,Stereoselective synthesis of HR 780 a new highly potent HMG-CoA reductase inhibitor.Tetrahedron Letters,1990,31(18):2545-2548.
34.Brower PL,Butler DE,Deering CF,Le TV,Millar A,Nanninga TN,Roth BD,The synthesis of(4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate,a key intermediate for the preparation of CI-981,a highly potent,tissue selective inhibitor of HMG-CoA reductase.Tetrahedron Letters,1992,33(17):2279-2282.
35.Butler DE,Le TV,Millar A,Process for the synthesis of(SR)-1,1-dimethylethyl-6-cyano-5-hydroxy-3-oxo-hexanoate.US 5155251,1992.
36.CHO Y-H,Process for producing optically pure β-hydroxy-ketoester derivatives.WO 02/096915,2002.
37.Tempkin O,Abel S,Chen C-P,Underwood R,Prasad K,Chen K-M,Repic O,Blacklock TJ,Asymmetric synthesis of 3,5-dihydroxy-6(E)-heptenoate-containing HMG-CoA reductase inhibitors.Tetrahedron,1997,53(31):10659-10670.
38.Lynch JE,Volante RP,Wattley RV,Shinkai I,Synthesis of an HNG-CoA reductase inhibitor;a diastereoselective aldol approach.Tetrahedron letters,1987,28(13):1385-1388.
39.Beck G,Jendralla H,Kesseler K,Practical Large-Scale Synthesis of Tert-Butyl (3R,SS)-6-Hydroxy-3,5-O-lsopropylidene-3,5-Dihydroxyhexanoate:Essential Building-Block for Hmg-CoA Reductase Inhibitors.Synthesis-Stuttgart,1995,(8):1014-1018.
40.Hiyama T,Minami T,Takahashi K,Synthesis of Artificial HMG-CoA Reductase Inhibitors Based on the Olefination Strategy.Bull.Chem.Soc.Jpn.1995,68:364-372.
41.Minami T,Takahashi K,Hiyama T,Stereoselective reduction of β,δ-diketo esters derived from tartaric acid.Tetrahedron letters,1993,34(3):513-516.
42.Urabe H,Matsuka T,Sato F,New Chiral Blocks for Introducing the Side Chain of HMG-CoA Reductase Inhibitors.Tetrahedron letters,1992,33(29):4183-4186.
43.Madec J,Pfister X,Phansavath P,Ratovelomanana V,Genet JP,Asymmetric hydrogenation reactions using a practical in situ generation of chiral ruthenium-diphosphine catalysts from anhydrous RuCl_3.Tetrahedron,2001,57(13):2563-2568.
44.Qiu LQ,Qi JY,Pai CC,Chan SS,Zhou ZY,Choi MCK,Chan ASC,Synthesis of novel diastereomeric diphosphine ligands and their applications in asymmetric hydrogenation reactions.Organic Letters,2002,4(26):4599-4602.
45.Everaere K,Franceschini N,Mortreux A,Carpentier JF,Diastereoselective synthesis of syn-3,5-dihydroxyesters via ruthenium-catalyzed asymmetric transfer hydrogenation.Tetrahedron Letters,2002,43(14):2569-2571.
46.Blandin V,Carpentier JF,Mortreux A,One-pot and sequential asymmetric hydrogenation of beta,delta-diketoesters into functionalized 1,3-diols:From anti-to syn-stereoselectivity.European Journal of Organic Chemistry,1999,(12):3421-3427.
47.Tararov VI,Koenig G,Boerner A,Synthesis and highly stereoselective hydrogenation of the statin precursor ethyl(5S)-5,6-isopropylidenedioxy-3-oxohexanoate.Advanced Synthesis &Catalysis,2006,348(18):2633-2644.
48.Stokker GE,Synthesis of L-669,262,a Potent HMG-CoA Reductase Inhibitor.J.Org.Chem.1994,59(20):5983-5986.
49.Honda T,Ono S,Mizutani H,Hallinan KO,Enantioselective synthesis of the lactone moiety of HMG-CoA reductase inhibitor:stereoseleetive synthesis of(+)-(4R,6R)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one.Tetrahedron:Asymmetry,1997,8(2):181-184.
50.Radl S,A new way to tert-butyi[(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate,a key intermediate of atorvastatin synthesis.Synthetic Communications,2003,33(13):2275-2283.
51.Masaru Mitsuda A,makoto Miyazaki A,Kenji Inoue K,Proess for producing 6-cyanomethyl-1,3-dioxane-4-acetic acid derivatives.US 6344569,2002.
52.Daniel M,Michael W,Natascha S,Process for the preparation of(4-hydroxy-6-oxotetrahydropyran -2-yl)acetonitrile and derivatives thereof.WO 2004/096788,2004.
53.Ghosh AK,Lei H,Chelation-Controlled Reduction:Stereoselective Formation of syn-1,3-Diols and Synthesis of Compactin and Mevinolin Lactone.J.Org.Chem.2002,67(25):8783-8788.
54.Scheffler J-L,Bette V,Mortreux A,Nowogrocki G,Carpentier J-F,Preparation and stereoselective hydrogenation of chiral(4-hydroxy-tetrafuranylidene)carboxylates:a new formal entry to functional anti-and syn-3,5-dihydroxyesters.Tetrahedron letters,2002,43:2679-2682.
55.Zdenko C Process for the preparation of statins and tetrahydropyranone intermediates.WO2007/039287,2007.
56.Santaniello E,Ferraboschi P,The Biocatalytic Approach to the Preparation of Enatiopure Chiral Building Blocks.Chemical Reviews,1992,92:1071-1140.
57.Mueller M,Chemoenzymatic synthesis of building blocks for statin side chains.Angewandte Chemie,International Edition,2005,44(3):362-365.
58.Muller M,Wolberg M,Schubert T,Hummel W,Enzyme-catalyzed regio-and enantioselective ketone reductions.Adv Biochem Engin/Biotechnol,2005,92:261-287.
59.Jiang B,Liu J-F,Zhao S-Y,Enantioselective Synthesis for the Antipodes of Slagenins B and C:Establishment of Absolute Stereochemistry.Org.Lett.2001,3(25):4011-4013.
60.Zhou BN,Gopalan AS,VanMiddlesworth F,Shieh WR,Sih CJ,Stereochemical control of yeast reductions.1.Asymmetric synthesis of L-carnitine.J.Am.Chem.Soc.1983,105(18):5925-5926.
61.John DS,Dehydrogenases and Transaminases in Asymmetric Synthesis.Curr.Opin.Chem.Biol.2001,5:120-129.
62.杨忠华,姚善泾,水相中酵母细胞催化 4-氯-乙酰乙酸乙醣不对称还原反应.催化学报,2004,25(6):434-438.
63.黄泱,吴坚平,杨立荣,CHBE的酶催化手性拆分反应条件的研究.第二届生物化工学术会议论文集,杭州 2002:340-345.
64.钟萍,孙志浩,生物催化不对称还原方法生产(S)-4-氯-3-羟基丁酸乙酯.过程工程学报,2005,5(6):665-669.
65.孙志浩,何军邀,生物催化制备光学活性 4-氯-3-羟基丁酸酯研究进展.化工进展,2006,25(6):623-628.
66.Itoh N,Matsuda M,Mabuchi M,Dairi T,Wang J,Chiral alcohol production by NADH-dependent phenylacetaldehyde reductase coupled with in situ regeneration of NADH.Eur.J.Biochem.2002,269(9):2394-2402.
67.Shimizu S,Kataoka M,Katoh M,Morikawa T,Stereoselective Reduction of Ethyl 4-Chloro-3-Oxobutanoate by a Microbial Aldehyde Reductase in an Organic Solvent-Water Diphasic System.Appl.Environ.Microbiol.1990,56(8):2374-2377.
68.Shimizu S,Kataoka M,Kita K,Chiral alcohol synthesis with yeast carbonyl reductases.J.Mol.Catal.B:Enzymatic 1998,5:321-325
69.Yasohara Y,Kizaki N,Hasegawa J,Takahashi S,Wada M,Kataoka M,Shimizu S,Synthesis of optically active ethyl 4-chloro-3-hydroxybutanoate by microbial reduction.Appl.Microbiol.Biotechnol.1999,51(6):847-851.
70.Kataoka M,Rohani L,Yamamoto K,Wada M,Kawabata H,Kita K,Yanase H,Shimizu S,Enzymatic production of ethyl(R)-4-chloro-3-hydroxybutanoate:asymmetric reduction of ethyl 4-chloro-3-oxobutanoate by an Escherichia coil transformant expressing the aldehyde reductase gene from yeast.Appl.Microbiol.Biotechnol.1997,48(6):699-703.
71.Kataoka M,Rohani L,Wada M,Kita K,Yanase H,Urabe I,Shimizu S,Escherichia coli transformant expressing the glucose dehydrogenase gene from Bacillus megaterium as a cofactor regenerator in a chiral alcohol production system.Biosci.Biotechnol.Biochem.1998,62(1):167-169.
72.Yasohara Y,Kizaki N,Hasegawa J,Wada M,Kataoka M,Shimizu S,Molecular cloning and overexpression of the gene encoding an NADPH-dependent carbonyl reductase from Candida magnoliae,involved in stereoselective reduction of ethyl 4-chloro-3-oxobutanoate.Biosci.Biotechnol.Biochem.2000,64(7):1430-1436.
73.Kizaki N,Yasohara Y,Hasegawa J,Wada M,Kataoka M,Shimizu S,Synthesis of optically pure ethyl(S)-4-chloro-3-hydroxybutanoate by Eseherichia coli transformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genes.Appl.Microbiol.Biotechnol.2001,55(5):590-595.
74.Baldwin JJ,Raab AW,Mender K,Arison BH,McClure DE,Synthesis of(R)-and (S)-Epichlorohydrin.J.Org.Chem.1978,43:4876-4878.
75.Kasai N,Tsujimura K,Unoura K,Suzuki T,Preparation of(S)-2,3-dichloro-1-propanol by Pseudomonas sp.and its use in the synthesis of(R)-epichlorohydrin.J.Indust.Microbiol.1992,9:97-100.
76.Kasai hi,Tsujimura K,Unoura K,Suzuki T,Degradation of 2,3-dichloro-1-propanol by a Pseudomonas sp.Agric.Biol.Chem.1990,54:3185-3190.
77.Patel RN,Banerjee A,McNamee CG,D Brzozowski,Hanson RL,Szarka L,Enantioselective microbial reduction of 3,5-dioxo-6-(benzyloxy)hexanoic acid,ethyl ester.Enzyme Microb.Technol.1993,15:1014-1021.
78.Patel RN,McNamee CG,Banerjee A,Szarka L,Stereoselective microbial or enzymatic reduction of 3,5-dioxo esters to 3-hydroxy-5-oxo,3-oxo-5-hydroxy,and 3,5-dihydroxy esters.EP569998,1993.
79.Guo Z,Chen Y,Goswami A,Hanson RL,Patel RN,Synthesis of ethyl and t-butyl (3R,SS)-dihydroxy-6-benzyloxy hexanoates via diastereo-and enantioselective microbial reduction.Tetrahedron:Asymmetry,2006,17:1589-1602.
80.Muller M,Wolberg M,Hummel W,Wandrey C,Method of reducing keto-carboxylic acids and their esters.WO0104336,2001.
81.Wolberg M,Hummel W,Wandrey C,Muller M,Highly regio-and enantioselective reduction of 3,5-dioxocarboxylate.Angew.Chem.Int.Ed.2000,39(23):4306-4307.
82.Wolberg M,Hummel W,Muller M,Biocatalytic reduction of β,δ-diketo esters:a highly stereoselective approach to all four stereoisomers of a chlorinated β,δ-dihydroxy hexanoate.Chem.Eur.J.2001,7(21):4562-4571.
83.Wolberg M,Kaluzna IA,Muller M,Stewart JD,Regio and enantioselective reduction of t-butyl 6-chloro-3,5-dioxohexanoate with baker's yeast.Tetrahedron:Asymmetry,2004,15:2825-2828.
84.Kizaki N,Yamada Y,Yasohara Y,Nishiyama A,Process for the preparation of optically active 2-[6-(hydroxymethyl)-1,3-dioxan-4-yl]acetic acid derivatives.EP 1024139,2000.
85.Reeve CD,Reduction of ketone groups.WO97/00968,1997.
86.Blacker A J,Holt RA,Reeve CD,Process for the preparation of dihydroxy esters and derivatives thereof.WO 011085975,2001.
87.Reeve CD,Enzymatic reduction of ketone groups in 6-cyano-3,5-dihydroxy-hexanoic alkyl ester.US6001615,1999.
88.Kalesse M,Eh M,Enantioselective Synthesis of the C1-C9 Segment of Bryostatin by Kinetic Resolution of Racemic 13-Keto Esters.Tetrahedron Lett.1996,37(11):1767-1770.
89.Bonini C,Pucci P,Viggiani L,A remarkable short synthesis of optically active mevinic acid analogs by biocatalytic lactonization of syn-3,5-dihydroxy esters,J.Org.Chem.1991,56(12):1050-4052.
90.Bonini C,Cazzato C,Cernia E,Palocci C,Soro S,Viggiani L,Lipase enhanced catalytic efficiency in lactonisation reactions,Journal of Molecular Catalysis B:Enzymatic,2005,16:1-5.
91.Gijsen HJM,Wong C-H,Unprecedented asymmetric aldol reactions with three aldehyde substrates catalyzed by 2-deoxyribose-5-phosphate aldolase.J.Am.Chem.Soc.1994,116:8422-8423.
92.Kierkels JGT,Mink D,Panke S,Lommen FAM,Heemskerk D,Process for the preparation of 2,4-dideoxyhexoses and 2,4,6-trideoxyhexoses.WO 03/006656,2003.
93.Greenberg WA,Varvak A,Hanson SR,Wong K,Huang H,Chen P,Burk MJ,Development of an efficient,scalable,aldolase-catalyzed process for enantioselective synthesis of statin intermediates.J.Proc.Natl.Acad.Sci.U.S.A.2004,101:5788-5793.
1.Brower PL,Butler DE,Deering CF,Le TV,Millar A,Nanninga TN and Roth BD,The synthesis of(4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate,a key intermediate for the preparation of CI-981,a highly potent,tissue selective inhibitor of HMG-CoA reduetase,Tetrahedron Letters 1992,33(17):2279-2282.
2.Butler DE,Le TV and Millar A,Process for the synthesis of(5R)-1,1-dimethylethyl-6-cyano-5-hydroxy-3-oxo-hexanoate,US 5155251,1992.
3.Cho Y-H,Process for producing optically pure β-hydroxy-ketoester derivatives,WO 02096915,2002.
4.Thottathil J K,Pendri Y,Li W-S and Kronenthal DR,Process for the preparation of 1,3-dioxane derivatives useful in the preparation of HMG-CoA,US5278313,1994.
5.Scheffler J-L,Bette V,Mortreux A,Nowogrocki G and Carpentier J-F,Preparation and stereoselective hydrogenation of chiral(4-hydroxy-tetrafuranylidene)carboxylates:a new formal entry to functional anti-and syn-3,5-dihydroxyesters,Tetrahedron letters 2002,43:2679-2682.
6.David L and John WA,Continuous process for the cyanation of hydrogenated beta-ketoesters,WO 03097581,2003.
7.Kim Y-J,Bemstein MP and Collum DB,On the Structure and Reactivity of Lithium Diisopropylamide(LDA)in Carboxamide Enolates Hydrocarbon Solutions.Formation of Unsolvated Ketone,Ester,and Carboxamide Enolates,J.Org.Chem.1991,56:4435-4439.
1.Konno H,Toshiro E,Hinoda N,An epoxide ring-opening reaction via hypervalent silicate intermediate:synthesis of statine,Synthesis 2003,14:2161-2164.
2.Benedetti F,Berti F,Norbedo S,Ring-opening of epoxy alcohols by diethylaluminium cyanide.Regio-and stereoselective synthesis of 1-cyano-2,3-diols,Tetrahedron Lett.1999,37:5477-5478.
3.Philips KD,Zemlicka J,Horwitz JP,Unsaturated sugars.1.Decarboxylative elimination of methyl 2,3-di-O-benzyl-a-D-glucopyranosiduronic acid to methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside,Carbohydr.Res.1973,30:281-286.
4.Buenadicha FL,Bartolome MT,Aguirre MJ,Avendano C,Sollhuber M,New findings in the alkylation and N-deprotection of(4S)-4-methyl-2-benzyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones,Tetrahedron:Asymmetry 1998,9:483-501.
5.Rodebaugh R,Debenham JS,Fraser-Reid B,Debenzylation of complex oligosaccharides using ferric chloride,Tetrahedron Lett.1996,37:5477-5478.
6.Leuenberger HGW,Interrelations of chemistry and biotechnology.I.Biotransformation-a useful tool in organic chemistry,Pure Appl.Chem.1990,62:753.
7.Zhang J,Wu JP,Yang LR,The kinetic study on lipase-catalyzed asymmetric alcoholysis of α-cyano-benzyl acetate in organic media,Journal of Molecular Catalysis B:Enzymatic 2004,31:67-72.
8.Kamal A,Khanna GBR,A facile preparation of β-hydroxy nitriles and their enzymic resolution with lipases,Tetrahedron:Asymmetry 2001,12:405-410.
9.Itoh T,Tagaki Y,Murakami T,Hiyama Y,Tsukube H,Crown ethers as regulators of enzymic reactions:Enhanced reaction rate and enantioselectivity in lipase-catalyzed hydrolysis of 2-cyano-1-methylethyl acetate,J.Org.Chem.1996,61:2158-2163.
10.Itoh T,Takagi Y,Nishiyama S,Enhanced enantioselectivity of an enzymatic reaction by the sulfur functional group.A simple preparation of optically active β-hydroxy nitriles using a lipase,J.Org.Chem.1991,56:1521-1524.
11.Partali V,Waagen V,Alivik T,Anthonsen T,Enzymic resolution of butanoic esters of 1-phenylmethyl and 1-(2-phenylethyl)ethers of 3-chloro-1,2-propanediol,Tetrahedron: Asymmetry 1993,4:961-968.
12.Hansen TV,Waagen V,Partali V,Anthonsen HW,Anthonsen T,Cosolvent enhancement of enantioselectivity in lipase-catalyzed hydrolysis of racemic esters.A process for production of homochiral C-3 building blocks using lipase B from Candida antarctica,Tetrahedron:Asymmetry 1995,6:499-504.
13.Beck G,Jendralla H,Kesseler K,Practical large scale synthesis of tert-butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate:Essential building block for HMG-CoA reductase inhibitors,Synthesis 1995:1014-1018.
14.Narkunan K,Uang BJ,Synthesis of δ-hydroxy β-oxo esters using sonochemical Blaise reaction,Synthesis 1998:1713-1714.
15.Evans DA,Kozlowski MC,Murry JA,Burgey CS,Campos KR,Connell BT,Staples RJ,C2-Symmetric Copper(Ⅱ)Complexes as Chiral Lewis Acids.Scope and Mechanism of Catalytic Enantioselective Aidol Additions of Enolsilanes to(Benzyloxy)acetaldehyde,J.Am.Chem.Soc.1999,121:669-685.
16.Klibanov AM,Improving enzymes by using them in organic solvents,Nature 2001,409:241-246.
17.Carrea G,Riva S,Properties and synthetic applications of enzymes in organic solvents,Angew Chem.Int.Ed.2000,39:2226-2254.
18.Naemura K,Murata M,Tanaka R,Yano M,Hirose K,Tobe Y,Enantioselective acylation of primary and secondary alcohols catalyzed by lipase QL from Alcaligenes sp.:a predictive active site model for lipase QL to identify which enantiomer of an alcohol reacts faster in this acylation,Tetrahedron:Asymmetry 1996,7:3285-3294.
19.Kim M-J,Choi Y,Lipase-catalyzed enantioselective transesterification of O-trityl 1,2-diols.Practical synthesis of(R)-tritylglycidol,J.Org.Chem.1992,57:1605-1607.
20.Kazlauskas RJ,Weissfloch ANE,Rappaport AT.,Cuecia LA,A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase,lipase from Pseudomonas cepacia,and lipase from Candida rugosa,J.Org.Chem.1991,56:2656-2665.
21.Tsujigami T,Sugai T,Ohta H,Microbial asymmetric reduction of α-hydroxy ketones in the anti-Prelog selectivity,Tetrahedron:Asymmetry 2001,12:2543-2549.
22.Borah JC,Gogoi S,Boruwa J,Barua NC,A highly efficient synthesis of the C-13side-chain of taxol using Shibasaki's asymmetric Henry reaction,Tetrahedron Lett.2001,45:3689-3691.
23.Brugat N,Duran J,Polo A,Real J,A,-L A,Piniella JF,Synthesis and characterization of a new chiral phosphinothiol ligand and its pailadium(Ⅱ)complexes,Tetrahedron:Asymmetry 2002,13:569-577.
24.Matsuyarna K,Ikunaka M,A practical enantioselective synthesis of (S)-3-hydroxytetradecanoic acid,Tetrahedron:Asymmetry 1999,10:2945-2950.
25.Langer SH,Connell S,Wender I,Preparation and properties of trimethylsilyl ethers and related compounds,J.Org.Chem.1958,23:50-58.
26.House H,Czuba L J,Gall M,Oimstend HD,Chemistry of carbonions.ⅩⅧ.Preparation of trimethylsilyl enol ethers,J.Org.Chem.1969,34:2324-2336.
27.Olah GA,Gupta BGB,Narang SC,Malhotra R,Synthesis methods and reactions.71.Chlorotrimethylsilane and tert-butyl dimethylsilyi chloride/lithium sulfide,mild and efficient silylating regents,J.Org.Chem.1979,44:4272-4575.
28.Shin HS,Choi BS,Lee KK,Choi H-W,Chang JH,Lee KW,Nam DH,Kim N-S,Efficient Activation of Zinc:Application of the Blaise Reaction to an Expedient Synthesis of a Statin Intermediate,Synthesis 2004:2629-2632.
29.Hannick SM,Kishi Y,An improved procedure for the Blaise reaction:a short,practical route to the key intermediates of the saxitoxin synthesis,J.Org.Chem.1983,48:3833-3835.
1.Radl S,A new way to tea-butyl[(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]actetate,a key intermediate of atorvastatin synthesis.Synthetic Commun,2003,33(13):2275-2283.
2.Brower PL,Butler DE,Deering CF,Le TV,Millar A,Nanninga TN and Roth BD,The synthesis of(3R,5S)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate,a key intermediate for the preparation of CI-981,a highly potent,tissue selective inhibitor of HMG-CoA reductase,Tetrahedron Lett.1992,33:2279-2282
3.Beck G,Jendralla H and Kesseler K,Practical Large-Scale Synthesis of Tea-Butyl (3R,5S)-6-Hydroxy-3,5-O-Isopropylidene-3,5-Dihydroxyhexanoate:Essential Building-Block for Hmg-CoA Reductase Inhibitors,Synthesis 1995,1014-1018
4 Wess G,Kesseler K,Baader E,Bartmann W,Beck G,Bergmann A,Jendralla H,Bock K,Holzstein O,Kleine H and Schnierer M,Stereoselective synthesis of HR 780 a new highly potent HMG-CoA reduetase inhibitor,Tetrahedron Lett.1990,31:2545-2548.
5.Thottathil J K,Pendri Y,Li W-S and Kronenthal DR,Process for the preparation of 1,3-dioxane derivatives useful in the preparation of HMG-CoA,US5278313,1994.
6.Urabe H,Matsuka T and Sato F,New Chiral Blocks for Introducing the Side Chain of HMG-CoA Reduetase Inhibitors,Tetrahedron Lett.1992,33:4183-4186.
1.Hoffman WF,Smith RL and Willard AK,Antihypercholesterolemic compounds,US 4444784,1984.
2.Baumann KL,Butler DE,Deering CF,Mennen KE,Millar A,Nanninga TN,Palmer CW and Roth BD,The convergent synthesis of CI-981,an optically active,highly potent,tissue selective inhibitor of HMG-CoA reductase,Tetrahedron Lett.1992,33:2283-2284.
3.Istvan ES and Deisenhofer J,Structural Mechanism for Statin Inhibition of HMG-CoA Reductase,Science 2001,292:1160-1164.
4.(a)Konoike T,Okada T and Araki Y,Optical Resolution of 3-(Silyloxy)glutaric Acid Half Esters and Their Utilization for Enantioconvergent Synthesis of a HMG-CoA Reductase Inhibitor,J.Org.Chem.1998,63,3037-3040;
(b)Wess G,Kesseler K,Baader E,Bartmann W,Beck G,Bergmann A,Jendralla H,Bock K,Holzstein O,Kleine H and Schnierer M,Stereoselective synthesis of HR 780 a new highly potent HMG-CoA reductase inhibitor,Tetrahedron Lett.1990,31:2545-2548;
(c)Konoike T and Araki Y,Practical Synthesis of Chiral Synthons for the Preparation of HMG-CoA Reductase Inhibitors,J.Org.Chem.1994,59:7849-7854;
(c)Brower PL,Butler DE,Deering CF,Le TV,Millar A,Nanninga TN and Roth BD,The synthesis of (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate,a key intermediate for the preparation of CI-981,a highly potent,tissue selective inhibitor of HMG-CoA reductase,Tetrahedron Lett.1992,33:2279-2282;
(d)Cho Y-H,Roh KR,Shin JH,Chun JP,Yu HS and Cho C-W,Process for producing optically pure β-hydroxy-ketoester derivatives,WO 2002096915,2002.
5.(a)Tempkin O,Abel S,Chen C-P,Underwood R,Prasad K,Chen K-M,Repic O and Blacklock T J,Asymmetric synthesis of 3,5-dihydroxy-6(E)-heptenoate-containing HMG-CoA reductase inhibitors,Tetrahedron 1997,53:10659-10670;
(b)Lynch JE,Volante RP,Wattley RV and Shinkai I,Synthesis of an HNG-CoA reductase inhibitor;a diastereoselective aldol approach,Tetrahedron Lett.1987,28:1385-1387;
(c)Beck G,Jendralla H and Kesseler K,Practical Large-Scale Synthesis of Tert-Butyl(3R,5S)-6-Hydroxy-3,5-O-Isopropylidene-3,5-Dihydroxyhexanoate:Essential Building-Block for Hmg-CoA Reductase Inhibitors,Synthesis 1995,1014-1018;
(d)Hiyama T,Minami T and Takahashi K,Synthesis of Artificial HMG-CoA Reductase Inhibitors Based on the Olefination Strategy,Bull.Chem.Soc.Jpn.1995,68:364-372;
(e)Minami T,Takahashi K and Hiyama T,Stereoselective reduction of β,δ-diketo esters derived from tartaric acid,Tetrahedron lett.1993,34:513-516;
(f)Urabe H,Matsuka T and Sato F,New Chiral Blocks for Introducing the Side Chain of HMG-CoA Reductase Inhibitors,Tetrahedron Lett.1992,33:4153-4156;
(g)Evans DA,Trenkle WC,Zhang J and Burch JD,Synthesis and Confirmation of the Absolute Stereochemistry of the(-)-Aflastatin A C_9-C_(27)Degradation Polyol,Org.Lett.2005,7:3335-3338;
(H)Evans DA,Kozlowski MC,Murry JA,Burgey CS,Campos KR,Connell BT and Staples RJ,C_2-Symmetdc Copper(Ⅱ)Complexes as Chiral Lewis Acids,J.Am.Chem.Soc.1999,121:669-685.
6.Chen K-M,Hardtmann GE,Prasad K,Repic O and Shapiro M J,1,3-syn-diastereoselective reduction of β-hydroxyketones utilizing alkoxydialkylboranes,Tetrahedron Lett.1987,28:155-158.
7.(a)Wolberg M,Hummel W,Wandrey C and Muller M,Highly regio-and enantioselective reduction of 3,5-dioxocarboxylate,Angew.Chem.Int.Ed.2000,39:4306-4307;
(b)Wolberg M,Hummel W and Muller M,Biocatalytic reduction of β,δ-diketo esters:a highly stereoselective approach to all four stereoisomers of a chlorinated β,δ-dihydroxy hexanoate,Chem.Eur.J.2001,7:4562-4571;
(c)Wolberg M,Kaluzna I.A,Muller M and Stewart JD,Regio and enantioselective reduction of t-butyl 6-chloro-3,5-dioxohexanoate with baker's yeast,Tetrahedron:Asymmetry 2004,15:2825-2828.
8.(a)Everaere K,Franceschini N,Mortreux A and Carpentier JF,Diastereoselective synthesis of syn-3,5-dihydroxyesters via ruthenium-catalyzed asymmetric transfer hydrogenation,Tetrahedron Lett.2002,43:2569-2571;
(b)Blandin V,Carpentier JF and Mortreux A,One-pot and sequential asymmetric hydrogenation of beta,delta-diketoesters into functionalized 1,3-diols:From anti-to syn-stereoselectivity,Eur.J.Org.Chem.1999,3421-3427.
9.(a)Patel RN,Banerjee A,McNamee CG,D Brzozowski,Hanson RL and Szarka L,Stereoselective microbial or enzymatic reduction of 3,5-dioxo esters to 3-hydroxy-5-oxo,3-oxo-5-hydroxy,and 3,5-dihydroxy esters,Enzyme Microb.Technol.1993,15:1014-1021;
(b)Guo Z,Chen Y,Goswami A,Hanson RL and Patel RN,Synthesis of ethyl and t-butyl (3R,5S)-dihydroxy-6-benzyloxy hexanoates via diastereo-and enantioselective microbial reduction,Tetrahedron:Asymmetry 2006,17:1589-1602.
10.(a)Tsujigami T,Sugai T and Ohta H,Microbial asymmetric reduction of α-hydroxy ketones in the anti-Preiog selectivity,Tetrahedron:Asymmetry 2001,12:2543-2549;
(b)Borah J.C,Gogoi S,Boruwa J,Kalita B and Barua NC,A highly efficient synthesis of the C-13 side-chain of taxol using Shibasaki's asymmetric Henry reaction,Tetrahedron Lett.2004,45:3689-3691.
11.Brandes A,Eggert U and Hoffmann HMR,Synthesis of Acyclic,Multifunctionalized α,α'-Disecondary Ethers with Full Control of Chemo-,Regio-and Enantioselectivity,Synlett 1994,745-747.
12.(a)House H,Czuba L.J,Gall M and Olmstend HD,Chemistry of carbonions.ⅩⅧ.Preparation of trimethylsilyl enol ethers,J.Org.Chem.1969,34:2324-2336;
(b)Olah GA,Gupta BGB,Narang SC and Malhotra R,Synthesis methods and reactions.71.Chlorotrimethylsilane and tert-butyl dimethylsilyi chloride/lithium sulfide,mild and efficient silylating reagents,J.Orig.Chem.1979,44:4272-4275.
13.(a)Shin HS,Choi BS,Lee KK,Chang JH,Lee KW,Nam DH and Kim N-S,Efficient Activation of Zinc:Application of the Blaise Reaction to an Expedient Synthesis of a Statin Intermediate,Synthesis 2004,2629-2632;
(b)Hannick SM and Kishi Y,An improved procedure for the Blaise reaction:a short,practical route to the key intermediates of the saxitoxin synthesis,J.Org.Chem.1983,48:3833-2835.
14.(a)Gerald C and Sandrine G-L,Selective hydrolysis of anti-1,3-diol-acetonides for the differentiation of 1,3-anti and 1,3-syn diols,Tetrahedron Lett.2006,47:671-674;
(b)Bode SE,Muller M and Wolherg M,Diastereomer-Differentiating Hydrolysis of 1,3-Diol-Acetonides:A Simplified Procedure for the Separation of syn-and anti-1,3-Diols,Org.Lett.2002,4:619-621.
15.(a)Partali V,Waagen V and Alivik T,Enzymic resolution of butanoic esters of 1-phenylmethyl and 1-(2-phenylethyl)ethers of 3-chloro-1,2-propanediol,Tetrahedron:Asymmetry 1993,4:961-968;
(b)Hansen TV,Waagen V,Partali V,Anthonsen HW and Anthonsen T,Cosolvent enhancement of enantioselectivity in lipase-catalyzed hydrolysis of racemic esters.A process for production of homochiral C-3 building blocks using iipase B from Candida antarctica,Tetrahedron:Asymmetry 1995,6:499-504;
(c)Pederson RL,Liu KK-C,Rutan JF,Chen L and Wong C-H,Enzymes in organic synthesis:synthesis of highly enantiomerically pure 1,2-epoxy aldehydes,epoxy alcohols,thiirane,aziridine,and glyceraldehyde 3-phosphate,J.Org.Chem.1990,55:4897-901;
(d)Lundhaug K,Overbeeke PLA,Jongejan JA and Anthonsen T,Organic co-solvents restore the inherently high enantiomeric ratio of lipase B from Candida antarctica in hydrolytic resolution by relieving the enantiospecific inhibition of product alcohol,Tetrahedron:Asymmetry 1998,9:2851-2856;
(e)Nakamura Y,Matsumoto T,Nomoto F,Ueda M,Fukuda H and Kondo A,Enhancement of Activity of Lipase-Displaying Yeast Cells and Their Application to Optical Resolution of (R,S)-1-Benzyloxy-3-Chloro-2-Propyl Monosuccinate,Biotechnol.Prog.2006,22:998-1002.
16.Sun F,Xu G,Wu J and Yang L,Efficient lipase-catalyzed kinetic resolution of 4-arylmethoxy-3-hydroxybutanenitriles:application to an expedient synthesis of a statin intermediate,Tetrahedron:Asymmetry 2006,17:2907-2913.
17.a)Naemura K,Murata M,Tanaka R,Yano M,Hirose K and Tobe Y,Enantioselective acylation of primary and secondary alcohols catalyzed by lipase QL from Alcaligenes sp:a predictive active site model for lipase QL to identify which enantiomer of an alcohol reacts faster in this acylation,Tetrahedron:Asymmetry 1996,7:3285-3294;
(b)Kim M-J and Choi YK,Lipase-catalyzed enantioselective transesterification of O-trityl 1,2-diols.Practical synthesis of (R)-tritylglycidol,J.Org.Chem.1992,57:165-1607.
18.Philips KD,Zemlicka J and Horwitz JP,Unsaturated sugars.1.Decarboxylative elimination of methyl 2,3-di-O-benzyl-a-D-glucopyranosiduronic acid to methyl 2,3-di-O-benzyl-4-deoxy -β-L-threo-pent-4-enopyranoside,Carbohydr.Res.1973,30:281-286.
19.(a)Haubenstock H and Eliel EL,Reductions with Metal Hydrides.Ⅺ.Solvent Effect on the Stereochemistry of Reduction with Sodium Borohydride,J.Am.Chem.Soc.1962,84:2368-2371;
(b)Cieplak AS,Stereochemistry of Nucleophilic Addition to Cyclohexanone.The Importance of Two-Electron Stabilizing InteractionsJ.Am.Chem.Soc.1981,103,4540-4552.
1.Graul A,Castaner J.Atorvastatin.Drugs Fut.,1997,22:956-965.
2.Istvan E S,Deisenhofer J.Structural mechanism for statin inhibition of HMG-CoA reductase.Science,2001,292:1160-1164.
3.Brower P L,Butler D E,Deering C F et al.The synthesis of(4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate,a key intermediate for the preparation of CI-981,a highly potent,tissue selective inhibitor of HMG-CoA reductase.Tetrahedron Lett.,1992,33(17):2279-2283.
4.Baumann K L,Butler D E,Deering C F et al.The convergent synthesis of CI-981,an optically active,highly potent,tissue selective inhibitor of HMG-CoA reductase.Tetrahedron Lett.,1992,33(17):2283-2284.
5.Butler D E,Le T V,Millar A.Process for the synthesis of(5R)-1,1-dimethylethyl-6-cyano-5-hydroxy-3-oxo-hexanoate.US5155251,1992.
6.Radi S.A new way to tert-butyl[(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]actetate,a key intermediate of atorvastatin synthesis.Synthetic Commun,2003,33(13):2275-2283.
7.Shin H S,Choi B S,Lee K K et al.Efficient activation of zinc:Application of the blaise reaction to an expedient synthesis of a statin intermediate.Synthesis,2004,16:2629-2632.
8.Beck G,Jendralla H,Kesseler K.Practical large-Scale synthesis of Tert-butyl(3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate:Essential building-block for HMG-CoA reductase inhibitors.Synthesis,1995,8:1014-1018.
9.Wolberg M,Hummel W,Muller M.Biocatalytic reduction of β,δ-diketo esters:A highly stereoselective approach to all four stereoisomers of a chlorinated β,δ-hihydroxy hexanote.Chem.Eur.J.,2001,7(21):4562-4571.
10.Zlicar M.Process for the synthesis of rosuvastatin calcium using L-malic acid for the side chain chirality.WO2007017117,2007.
2.鄢华,高炜,他汀类药物作用和作用机制的新认识.临床内科杂志,2006,23(1):5-7.
3.Executive Summary of the Third Report of the National Cholesterol Education Program (NCEP)Expert Panel on Detection,Evaluation,and Treatment of High Blood Cholesterol in Adults(Adult Treatment Panel Ⅲ).JAMA,2001,285:2486-2497.
4.梁丽,采用他汀类药物进行更积极的降脂治疗.中国医学论坛 2001-10-18,第5版.
5.Endo A,Monacolin k,A new hypocholesterolemic agent produced by a monascus species.J Antibiot,1979,32(8):852-854.
6.Alberts AW,Chen J,Kuron G,Hunt V,Huff J,Hoffman C,Rothrock J,Lopez M,Joshua H,Harris E,Patchett A,Monaghan R,Curfie S,Stapley E,Albers-Schonherg G,Hensens O,Hirshfield J,Hoogsteen K,Liesch J,Springer J,Mevinolin:A highly potent competitive inhibitor of hydroxymethylglutaryl coenzyme-a reductase and a cholesterol lowering agent.Proc.Nati.Acad.Sci.,1980,77(12):3957-3961.
7.Hoffman WF,Albers AW,Anderson PS,Chen JS,Smith RL,Willard AK,3-Hydroxy-3-methylglutaryl-coenzyme A Reductase Inhibitors.4.Side Chain Esters Derivatives of Mevinolin.J.Med.Chem.,1986,29:849-852.
8.Serizawa N,Nakagawa K,Hanano K,Microbial hydroxylation of ML-236B(compaction)and monacolin K(MB-530B).J Antibiot.,1983,36(5):604-607.
9.Tarr L,Pravastatin:A "new" advance in lipid therapy,Scrip 1988,1356:22-23.
10.贺爱珍,胡迎富,丁娟,魏立新,氟伐他汀钠降脂疗效的临床观察.临床心血管病杂志,2001,17(1):37.
11.Baumann KL,Butler DE,Deering CF,Mermen KE,Miilar A,Nanninga TN,Palmer CW,Roth BD,The convergent synthesis of CI-981,an optically active,highly potent,tissue selective inhibitor of HMG-CoA reductase.Tetrahedron Letters,1992,33(17):2283-2284.
12.Quirk J,Thornton M,Kirkpatdck P,Rosuvastatin calcium.News & Analysis,2003,2:769-770.
13.何笑荣,邹定,姜文清,马捷,李金娥,降血脂新药匹伐他汀.中国新药杂志,2005,14(4):483-487.
14.Suzuki M,Iwasaki H,Fujikawa Y,Kitahara M,Sakashita M,Sakoda R,Synthesis and biological evaluations of quinoline-based HMG-CoA reductase inhibitors.Bioorganic &Medicinal Chemistry,2001,9(10):2727-2743.
15.杨亚莉,降血脂新药-西立伐他汀从市场撤出.中国药事,2001,5(15):342.
16.Bischoff H,Angerbauer R,Berder J,Cerivastatin:pharmacology of a novel synthetic and highly active HMG-CoA reductase inhibitor.Atherosclerosis,1997,135:119-130.
17.黄震华,新型调脂药物西立伐他汀.中国新药与临床杂志,2000,19(5):345-347.
18.Endo A,Kuroda M,Tsujita Y,ML-236A,ML-236B and ML-236C,New inhibitors of cholesterogenesis produced by penicillium citrinum,J Antibiot 1976,29(12):1346-1348.
19.Wattanasin S,Do HD,Bhongle N,Kathawala FG,Enantiomerie synthesis of the.beta.-lactone precursor of the HMG-CoA synthase inhibitor(+)-F-(244).J.Chem.Org.1993,58:1610-1612.
20.Stokker GE,Synthesis of L-669,262,a Potent HMG-CoA Reductase Inhibitor.J.Chem.Org.1994,59:5983-5986.
21.Inoue M,Nakada M,Structure Elucidation and Enantioselective Total Synthesis of the Potent HMG-CoA Reductase Inhibitor FR901512 via Catalytic Asymmetric Nozaki-Hiyama Reactions.J.Am.Chem.Soc.2007,129(14):4164-4165.
22.Konoike T,Okada T,Araki Y,Optical Resolution of 3-(Silyloxy)glutaric Acid Half Esters and Their Utilization for Enantioconvergent Synthesis of a HMG-CoA Reductase Inhibitor.J.Org.Chem.1998,63(9):3037-3040.
23.Wess G,Kramer W,Han XB,Bock K,Enhsen A,Glombik H,Baringhaus K-H,Boeger G,Urmann M,et al.,Synthesis and Biological Activity of Bile Acid-Derived HMG-CoA Reductase Inhibitors.The Role of 21-Methyl in Recognition of HMG-CoA Reduetase and the Ileal Bile Acid Transport System.J.Med.Chem.1994,37(20):3240-3246.
24.Zhang QY,Wan J,Xu X,Yang GF,Ren YL,Liu JJ,Wang H,Guo Y,Structure-Based Rational Quest for Potential Novel Inhibitors of Human HMG-CoA Reduetase by Combining CoMFA 3D QSAR Modeling and Virtual Screening.J.Comb.Chem.2007,9(1):131-138.
25.Istvan ES,Deisenhofer J,Structural Mechanism for Statin Inhibition of HMG-CoA Reduetase.Science,2001,292:1160-1164.
26.傅志君,尤启冬,唐伟方,李志裕,他汀类药物作用模式和构效关系研究进展.中国 药学杂志,2003,38(6):404-407.
27.蔡正艳,宁奇,周伟澄,HMG-CoA还原酶抑制剂的合成(上).中国医药工业杂志,2004,35(10):621-626.
28.蔡正艳,宁奇,周伟澄,HMG-CoA还原酶抑制剂的合成(下).中国医药工业杂志,2004,35(11):687-691.
29.陈碧珊,苏丽华,他汀类药物的研究进展.中国药房,2005,16(7):545-546.
30.蔡正艳,宁奇,周伟澄,氟伐他汀钠的合成.中国医药工业杂志,2007,38(2):73-75.
31.蔡伟,张国英,赵文镜,罗永慧,瑞舒伐他汀钙的合成.江苏药学与临床研究,2005,13(4):9-10.
32.Konoike T,Araki Y,Practical Synthesis of Chiral Synthons for the Preparation of HMG-CoA Reductase Inhibitors.J.Org.Chem.1994,59(25):7849-7854.
33.Wess G,Kesseler K,Baader E,Bartmann W,Beck G,Bergmann A,Jendralla H,Bock K,Holzstein O,Kleine H,Schnierer M,Stereoselective synthesis of HR 780 a new highly potent HMG-CoA reductase inhibitor.Tetrahedron Letters,1990,31(18):2545-2548.
34.Brower PL,Butler DE,Deering CF,Le TV,Millar A,Nanninga TN,Roth BD,The synthesis of(4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate,a key intermediate for the preparation of CI-981,a highly potent,tissue selective inhibitor of HMG-CoA reductase.Tetrahedron Letters,1992,33(17):2279-2282.
35.Butler DE,Le TV,Millar A,Process for the synthesis of(SR)-1,1-dimethylethyl-6-cyano-5-hydroxy-3-oxo-hexanoate.US 5155251,1992.
36.CHO Y-H,Process for producing optically pure β-hydroxy-ketoester derivatives.WO 02/096915,2002.
37.Tempkin O,Abel S,Chen C-P,Underwood R,Prasad K,Chen K-M,Repic O,Blacklock TJ,Asymmetric synthesis of 3,5-dihydroxy-6(E)-heptenoate-containing HMG-CoA reductase inhibitors.Tetrahedron,1997,53(31):10659-10670.
38.Lynch JE,Volante RP,Wattley RV,Shinkai I,Synthesis of an HNG-CoA reductase inhibitor;a diastereoselective aldol approach.Tetrahedron letters,1987,28(13):1385-1388.
39.Beck G,Jendralla H,Kesseler K,Practical Large-Scale Synthesis of Tert-Butyl (3R,SS)-6-Hydroxy-3,5-O-lsopropylidene-3,5-Dihydroxyhexanoate:Essential Building-Block for Hmg-CoA Reductase Inhibitors.Synthesis-Stuttgart,1995,(8):1014-1018.
40.Hiyama T,Minami T,Takahashi K,Synthesis of Artificial HMG-CoA Reductase Inhibitors Based on the Olefination Strategy.Bull.Chem.Soc.Jpn.1995,68:364-372.
41.Minami T,Takahashi K,Hiyama T,Stereoselective reduction of β,δ-diketo esters derived from tartaric acid.Tetrahedron letters,1993,34(3):513-516.
42.Urabe H,Matsuka T,Sato F,New Chiral Blocks for Introducing the Side Chain of HMG-CoA Reductase Inhibitors.Tetrahedron letters,1992,33(29):4183-4186.
43.Madec J,Pfister X,Phansavath P,Ratovelomanana V,Genet JP,Asymmetric hydrogenation reactions using a practical in situ generation of chiral ruthenium-diphosphine catalysts from anhydrous RuCl_3.Tetrahedron,2001,57(13):2563-2568.
44.Qiu LQ,Qi JY,Pai CC,Chan SS,Zhou ZY,Choi MCK,Chan ASC,Synthesis of novel diastereomeric diphosphine ligands and their applications in asymmetric hydrogenation reactions.Organic Letters,2002,4(26):4599-4602.
45.Everaere K,Franceschini N,Mortreux A,Carpentier JF,Diastereoselective synthesis of syn-3,5-dihydroxyesters via ruthenium-catalyzed asymmetric transfer hydrogenation.Tetrahedron Letters,2002,43(14):2569-2571.
46.Blandin V,Carpentier JF,Mortreux A,One-pot and sequential asymmetric hydrogenation of beta,delta-diketoesters into functionalized 1,3-diols:From anti-to syn-stereoselectivity.European Journal of Organic Chemistry,1999,(12):3421-3427.
47.Tararov VI,Koenig G,Boerner A,Synthesis and highly stereoselective hydrogenation of the statin precursor ethyl(5S)-5,6-isopropylidenedioxy-3-oxohexanoate.Advanced Synthesis &Catalysis,2006,348(18):2633-2644.
48.Stokker GE,Synthesis of L-669,262,a Potent HMG-CoA Reductase Inhibitor.J.Org.Chem.1994,59(20):5983-5986.
49.Honda T,Ono S,Mizutani H,Hallinan KO,Enantioselective synthesis of the lactone moiety of HMG-CoA reductase inhibitor:stereoseleetive synthesis of(+)-(4R,6R)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one.Tetrahedron:Asymmetry,1997,8(2):181-184.
50.Radl S,A new way to tert-butyi[(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate,a key intermediate of atorvastatin synthesis.Synthetic Communications,2003,33(13):2275-2283.
51.Masaru Mitsuda A,makoto Miyazaki A,Kenji Inoue K,Proess for producing 6-cyanomethyl-1,3-dioxane-4-acetic acid derivatives.US 6344569,2002.
52.Daniel M,Michael W,Natascha S,Process for the preparation of(4-hydroxy-6-oxotetrahydropyran -2-yl)acetonitrile and derivatives thereof.WO 2004/096788,2004.
53.Ghosh AK,Lei H,Chelation-Controlled Reduction:Stereoselective Formation of syn-1,3-Diols and Synthesis of Compactin and Mevinolin Lactone.J.Org.Chem.2002,67(25):8783-8788.
54.Scheffler J-L,Bette V,Mortreux A,Nowogrocki G,Carpentier J-F,Preparation and stereoselective hydrogenation of chiral(4-hydroxy-tetrafuranylidene)carboxylates:a new formal entry to functional anti-and syn-3,5-dihydroxyesters.Tetrahedron letters,2002,43:2679-2682.
55.Zdenko C Process for the preparation of statins and tetrahydropyranone intermediates.WO2007/039287,2007.
56.Santaniello E,Ferraboschi P,The Biocatalytic Approach to the Preparation of Enatiopure Chiral Building Blocks.Chemical Reviews,1992,92:1071-1140.
57.Mueller M,Chemoenzymatic synthesis of building blocks for statin side chains.Angewandte Chemie,International Edition,2005,44(3):362-365.
58.Muller M,Wolberg M,Schubert T,Hummel W,Enzyme-catalyzed regio-and enantioselective ketone reductions.Adv Biochem Engin/Biotechnol,2005,92:261-287.
59.Jiang B,Liu J-F,Zhao S-Y,Enantioselective Synthesis for the Antipodes of Slagenins B and C:Establishment of Absolute Stereochemistry.Org.Lett.2001,3(25):4011-4013.
60.Zhou BN,Gopalan AS,VanMiddlesworth F,Shieh WR,Sih CJ,Stereochemical control of yeast reductions.1.Asymmetric synthesis of L-carnitine.J.Am.Chem.Soc.1983,105(18):5925-5926.
61.John DS,Dehydrogenases and Transaminases in Asymmetric Synthesis.Curr.Opin.Chem.Biol.2001,5:120-129.
62.杨忠华,姚善泾,水相中酵母细胞催化 4-氯-乙酰乙酸乙醣不对称还原反应.催化学报,2004,25(6):434-438.
63.黄泱,吴坚平,杨立荣,CHBE的酶催化手性拆分反应条件的研究.第二届生物化工学术会议论文集,杭州 2002:340-345.
64.钟萍,孙志浩,生物催化不对称还原方法生产(S)-4-氯-3-羟基丁酸乙酯.过程工程学报,2005,5(6):665-669.
65.孙志浩,何军邀,生物催化制备光学活性 4-氯-3-羟基丁酸酯研究进展.化工进展,2006,25(6):623-628.
66.Itoh N,Matsuda M,Mabuchi M,Dairi T,Wang J,Chiral alcohol production by NADH-dependent phenylacetaldehyde reductase coupled with in situ regeneration of NADH.Eur.J.Biochem.2002,269(9):2394-2402.
67.Shimizu S,Kataoka M,Katoh M,Morikawa T,Stereoselective Reduction of Ethyl 4-Chloro-3-Oxobutanoate by a Microbial Aldehyde Reductase in an Organic Solvent-Water Diphasic System.Appl.Environ.Microbiol.1990,56(8):2374-2377.
68.Shimizu S,Kataoka M,Kita K,Chiral alcohol synthesis with yeast carbonyl reductases.J.Mol.Catal.B:Enzymatic 1998,5:321-325
69.Yasohara Y,Kizaki N,Hasegawa J,Takahashi S,Wada M,Kataoka M,Shimizu S,Synthesis of optically active ethyl 4-chloro-3-hydroxybutanoate by microbial reduction.Appl.Microbiol.Biotechnol.1999,51(6):847-851.
70.Kataoka M,Rohani L,Yamamoto K,Wada M,Kawabata H,Kita K,Yanase H,Shimizu S,Enzymatic production of ethyl(R)-4-chloro-3-hydroxybutanoate:asymmetric reduction of ethyl 4-chloro-3-oxobutanoate by an Escherichia coil transformant expressing the aldehyde reductase gene from yeast.Appl.Microbiol.Biotechnol.1997,48(6):699-703.
71.Kataoka M,Rohani L,Wada M,Kita K,Yanase H,Urabe I,Shimizu S,Escherichia coli transformant expressing the glucose dehydrogenase gene from Bacillus megaterium as a cofactor regenerator in a chiral alcohol production system.Biosci.Biotechnol.Biochem.1998,62(1):167-169.
72.Yasohara Y,Kizaki N,Hasegawa J,Wada M,Kataoka M,Shimizu S,Molecular cloning and overexpression of the gene encoding an NADPH-dependent carbonyl reductase from Candida magnoliae,involved in stereoselective reduction of ethyl 4-chloro-3-oxobutanoate.Biosci.Biotechnol.Biochem.2000,64(7):1430-1436.
73.Kizaki N,Yasohara Y,Hasegawa J,Wada M,Kataoka M,Shimizu S,Synthesis of optically pure ethyl(S)-4-chloro-3-hydroxybutanoate by Eseherichia coli transformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genes.Appl.Microbiol.Biotechnol.2001,55(5):590-595.
74.Baldwin JJ,Raab AW,Mender K,Arison BH,McClure DE,Synthesis of(R)-and (S)-Epichlorohydrin.J.Org.Chem.1978,43:4876-4878.
75.Kasai N,Tsujimura K,Unoura K,Suzuki T,Preparation of(S)-2,3-dichloro-1-propanol by Pseudomonas sp.and its use in the synthesis of(R)-epichlorohydrin.J.Indust.Microbiol.1992,9:97-100.
76.Kasai hi,Tsujimura K,Unoura K,Suzuki T,Degradation of 2,3-dichloro-1-propanol by a Pseudomonas sp.Agric.Biol.Chem.1990,54:3185-3190.
77.Patel RN,Banerjee A,McNamee CG,D Brzozowski,Hanson RL,Szarka L,Enantioselective microbial reduction of 3,5-dioxo-6-(benzyloxy)hexanoic acid,ethyl ester.Enzyme Microb.Technol.1993,15:1014-1021.
78.Patel RN,McNamee CG,Banerjee A,Szarka L,Stereoselective microbial or enzymatic reduction of 3,5-dioxo esters to 3-hydroxy-5-oxo,3-oxo-5-hydroxy,and 3,5-dihydroxy esters.EP569998,1993.
79.Guo Z,Chen Y,Goswami A,Hanson RL,Patel RN,Synthesis of ethyl and t-butyl (3R,SS)-dihydroxy-6-benzyloxy hexanoates via diastereo-and enantioselective microbial reduction.Tetrahedron:Asymmetry,2006,17:1589-1602.
80.Muller M,Wolberg M,Hummel W,Wandrey C,Method of reducing keto-carboxylic acids and their esters.WO0104336,2001.
81.Wolberg M,Hummel W,Wandrey C,Muller M,Highly regio-and enantioselective reduction of 3,5-dioxocarboxylate.Angew.Chem.Int.Ed.2000,39(23):4306-4307.
82.Wolberg M,Hummel W,Muller M,Biocatalytic reduction of β,δ-diketo esters:a highly stereoselective approach to all four stereoisomers of a chlorinated β,δ-dihydroxy hexanoate.Chem.Eur.J.2001,7(21):4562-4571.
83.Wolberg M,Kaluzna IA,Muller M,Stewart JD,Regio and enantioselective reduction of t-butyl 6-chloro-3,5-dioxohexanoate with baker's yeast.Tetrahedron:Asymmetry,2004,15:2825-2828.
84.Kizaki N,Yamada Y,Yasohara Y,Nishiyama A,Process for the preparation of optically active 2-[6-(hydroxymethyl)-1,3-dioxan-4-yl]acetic acid derivatives.EP 1024139,2000.
85.Reeve CD,Reduction of ketone groups.WO97/00968,1997.
86.Blacker A J,Holt RA,Reeve CD,Process for the preparation of dihydroxy esters and derivatives thereof.WO 011085975,2001.
87.Reeve CD,Enzymatic reduction of ketone groups in 6-cyano-3,5-dihydroxy-hexanoic alkyl ester.US6001615,1999.
88.Kalesse M,Eh M,Enantioselective Synthesis of the C1-C9 Segment of Bryostatin by Kinetic Resolution of Racemic 13-Keto Esters.Tetrahedron Lett.1996,37(11):1767-1770.
89.Bonini C,Pucci P,Viggiani L,A remarkable short synthesis of optically active mevinic acid analogs by biocatalytic lactonization of syn-3,5-dihydroxy esters,J.Org.Chem.1991,56(12):1050-4052.
90.Bonini C,Cazzato C,Cernia E,Palocci C,Soro S,Viggiani L,Lipase enhanced catalytic efficiency in lactonisation reactions,Journal of Molecular Catalysis B:Enzymatic,2005,16:1-5.
91.Gijsen HJM,Wong C-H,Unprecedented asymmetric aldol reactions with three aldehyde substrates catalyzed by 2-deoxyribose-5-phosphate aldolase.J.Am.Chem.Soc.1994,116:8422-8423.
92.Kierkels JGT,Mink D,Panke S,Lommen FAM,Heemskerk D,Process for the preparation of 2,4-dideoxyhexoses and 2,4,6-trideoxyhexoses.WO 03/006656,2003.
93.Greenberg WA,Varvak A,Hanson SR,Wong K,Huang H,Chen P,Burk MJ,Development of an efficient,scalable,aldolase-catalyzed process for enantioselective synthesis of statin intermediates.J.Proc.Natl.Acad.Sci.U.S.A.2004,101:5788-5793.
1.Brower PL,Butler DE,Deering CF,Le TV,Millar A,Nanninga TN and Roth BD,The synthesis of(4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate,a key intermediate for the preparation of CI-981,a highly potent,tissue selective inhibitor of HMG-CoA reduetase,Tetrahedron Letters 1992,33(17):2279-2282.
2.Butler DE,Le TV and Millar A,Process for the synthesis of(5R)-1,1-dimethylethyl-6-cyano-5-hydroxy-3-oxo-hexanoate,US 5155251,1992.
3.Cho Y-H,Process for producing optically pure β-hydroxy-ketoester derivatives,WO 02096915,2002.
4.Thottathil J K,Pendri Y,Li W-S and Kronenthal DR,Process for the preparation of 1,3-dioxane derivatives useful in the preparation of HMG-CoA,US5278313,1994.
5.Scheffler J-L,Bette V,Mortreux A,Nowogrocki G and Carpentier J-F,Preparation and stereoselective hydrogenation of chiral(4-hydroxy-tetrafuranylidene)carboxylates:a new formal entry to functional anti-and syn-3,5-dihydroxyesters,Tetrahedron letters 2002,43:2679-2682.
6.David L and John WA,Continuous process for the cyanation of hydrogenated beta-ketoesters,WO 03097581,2003.
7.Kim Y-J,Bemstein MP and Collum DB,On the Structure and Reactivity of Lithium Diisopropylamide(LDA)in Carboxamide Enolates Hydrocarbon Solutions.Formation of Unsolvated Ketone,Ester,and Carboxamide Enolates,J.Org.Chem.1991,56:4435-4439.
1.Konno H,Toshiro E,Hinoda N,An epoxide ring-opening reaction via hypervalent silicate intermediate:synthesis of statine,Synthesis 2003,14:2161-2164.
2.Benedetti F,Berti F,Norbedo S,Ring-opening of epoxy alcohols by diethylaluminium cyanide.Regio-and stereoselective synthesis of 1-cyano-2,3-diols,Tetrahedron Lett.1999,37:5477-5478.
3.Philips KD,Zemlicka J,Horwitz JP,Unsaturated sugars.1.Decarboxylative elimination of methyl 2,3-di-O-benzyl-a-D-glucopyranosiduronic acid to methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside,Carbohydr.Res.1973,30:281-286.
4.Buenadicha FL,Bartolome MT,Aguirre MJ,Avendano C,Sollhuber M,New findings in the alkylation and N-deprotection of(4S)-4-methyl-2-benzyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones,Tetrahedron:Asymmetry 1998,9:483-501.
5.Rodebaugh R,Debenham JS,Fraser-Reid B,Debenzylation of complex oligosaccharides using ferric chloride,Tetrahedron Lett.1996,37:5477-5478.
6.Leuenberger HGW,Interrelations of chemistry and biotechnology.I.Biotransformation-a useful tool in organic chemistry,Pure Appl.Chem.1990,62:753.
7.Zhang J,Wu JP,Yang LR,The kinetic study on lipase-catalyzed asymmetric alcoholysis of α-cyano-benzyl acetate in organic media,Journal of Molecular Catalysis B:Enzymatic 2004,31:67-72.
8.Kamal A,Khanna GBR,A facile preparation of β-hydroxy nitriles and their enzymic resolution with lipases,Tetrahedron:Asymmetry 2001,12:405-410.
9.Itoh T,Tagaki Y,Murakami T,Hiyama Y,Tsukube H,Crown ethers as regulators of enzymic reactions:Enhanced reaction rate and enantioselectivity in lipase-catalyzed hydrolysis of 2-cyano-1-methylethyl acetate,J.Org.Chem.1996,61:2158-2163.
10.Itoh T,Takagi Y,Nishiyama S,Enhanced enantioselectivity of an enzymatic reaction by the sulfur functional group.A simple preparation of optically active β-hydroxy nitriles using a lipase,J.Org.Chem.1991,56:1521-1524.
11.Partali V,Waagen V,Alivik T,Anthonsen T,Enzymic resolution of butanoic esters of 1-phenylmethyl and 1-(2-phenylethyl)ethers of 3-chloro-1,2-propanediol,Tetrahedron: Asymmetry 1993,4:961-968.
12.Hansen TV,Waagen V,Partali V,Anthonsen HW,Anthonsen T,Cosolvent enhancement of enantioselectivity in lipase-catalyzed hydrolysis of racemic esters.A process for production of homochiral C-3 building blocks using lipase B from Candida antarctica,Tetrahedron:Asymmetry 1995,6:499-504.
13.Beck G,Jendralla H,Kesseler K,Practical large scale synthesis of tert-butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate:Essential building block for HMG-CoA reductase inhibitors,Synthesis 1995:1014-1018.
14.Narkunan K,Uang BJ,Synthesis of δ-hydroxy β-oxo esters using sonochemical Blaise reaction,Synthesis 1998:1713-1714.
15.Evans DA,Kozlowski MC,Murry JA,Burgey CS,Campos KR,Connell BT,Staples RJ,C2-Symmetric Copper(Ⅱ)Complexes as Chiral Lewis Acids.Scope and Mechanism of Catalytic Enantioselective Aidol Additions of Enolsilanes to(Benzyloxy)acetaldehyde,J.Am.Chem.Soc.1999,121:669-685.
16.Klibanov AM,Improving enzymes by using them in organic solvents,Nature 2001,409:241-246.
17.Carrea G,Riva S,Properties and synthetic applications of enzymes in organic solvents,Angew Chem.Int.Ed.2000,39:2226-2254.
18.Naemura K,Murata M,Tanaka R,Yano M,Hirose K,Tobe Y,Enantioselective acylation of primary and secondary alcohols catalyzed by lipase QL from Alcaligenes sp.:a predictive active site model for lipase QL to identify which enantiomer of an alcohol reacts faster in this acylation,Tetrahedron:Asymmetry 1996,7:3285-3294.
19.Kim M-J,Choi Y,Lipase-catalyzed enantioselective transesterification of O-trityl 1,2-diols.Practical synthesis of(R)-tritylglycidol,J.Org.Chem.1992,57:1605-1607.
20.Kazlauskas RJ,Weissfloch ANE,Rappaport AT.,Cuecia LA,A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase,lipase from Pseudomonas cepacia,and lipase from Candida rugosa,J.Org.Chem.1991,56:2656-2665.
21.Tsujigami T,Sugai T,Ohta H,Microbial asymmetric reduction of α-hydroxy ketones in the anti-Prelog selectivity,Tetrahedron:Asymmetry 2001,12:2543-2549.
22.Borah JC,Gogoi S,Boruwa J,Barua NC,A highly efficient synthesis of the C-13side-chain of taxol using Shibasaki's asymmetric Henry reaction,Tetrahedron Lett.2001,45:3689-3691.
23.Brugat N,Duran J,Polo A,Real J,A,-L A,Piniella JF,Synthesis and characterization of a new chiral phosphinothiol ligand and its pailadium(Ⅱ)complexes,Tetrahedron:Asymmetry 2002,13:569-577.
24.Matsuyarna K,Ikunaka M,A practical enantioselective synthesis of (S)-3-hydroxytetradecanoic acid,Tetrahedron:Asymmetry 1999,10:2945-2950.
25.Langer SH,Connell S,Wender I,Preparation and properties of trimethylsilyl ethers and related compounds,J.Org.Chem.1958,23:50-58.
26.House H,Czuba L J,Gall M,Oimstend HD,Chemistry of carbonions.ⅩⅧ.Preparation of trimethylsilyl enol ethers,J.Org.Chem.1969,34:2324-2336.
27.Olah GA,Gupta BGB,Narang SC,Malhotra R,Synthesis methods and reactions.71.Chlorotrimethylsilane and tert-butyl dimethylsilyi chloride/lithium sulfide,mild and efficient silylating regents,J.Org.Chem.1979,44:4272-4575.
28.Shin HS,Choi BS,Lee KK,Choi H-W,Chang JH,Lee KW,Nam DH,Kim N-S,Efficient Activation of Zinc:Application of the Blaise Reaction to an Expedient Synthesis of a Statin Intermediate,Synthesis 2004:2629-2632.
29.Hannick SM,Kishi Y,An improved procedure for the Blaise reaction:a short,practical route to the key intermediates of the saxitoxin synthesis,J.Org.Chem.1983,48:3833-3835.
1.Radl S,A new way to tea-butyl[(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]actetate,a key intermediate of atorvastatin synthesis.Synthetic Commun,2003,33(13):2275-2283.
2.Brower PL,Butler DE,Deering CF,Le TV,Millar A,Nanninga TN and Roth BD,The synthesis of(3R,5S)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate,a key intermediate for the preparation of CI-981,a highly potent,tissue selective inhibitor of HMG-CoA reductase,Tetrahedron Lett.1992,33:2279-2282
3.Beck G,Jendralla H and Kesseler K,Practical Large-Scale Synthesis of Tea-Butyl (3R,5S)-6-Hydroxy-3,5-O-Isopropylidene-3,5-Dihydroxyhexanoate:Essential Building-Block for Hmg-CoA Reductase Inhibitors,Synthesis 1995,1014-1018
4 Wess G,Kesseler K,Baader E,Bartmann W,Beck G,Bergmann A,Jendralla H,Bock K,Holzstein O,Kleine H and Schnierer M,Stereoselective synthesis of HR 780 a new highly potent HMG-CoA reduetase inhibitor,Tetrahedron Lett.1990,31:2545-2548.
5.Thottathil J K,Pendri Y,Li W-S and Kronenthal DR,Process for the preparation of 1,3-dioxane derivatives useful in the preparation of HMG-CoA,US5278313,1994.
6.Urabe H,Matsuka T and Sato F,New Chiral Blocks for Introducing the Side Chain of HMG-CoA Reduetase Inhibitors,Tetrahedron Lett.1992,33:4183-4186.
1.Hoffman WF,Smith RL and Willard AK,Antihypercholesterolemic compounds,US 4444784,1984.
2.Baumann KL,Butler DE,Deering CF,Mennen KE,Millar A,Nanninga TN,Palmer CW and Roth BD,The convergent synthesis of CI-981,an optically active,highly potent,tissue selective inhibitor of HMG-CoA reductase,Tetrahedron Lett.1992,33:2283-2284.
3.Istvan ES and Deisenhofer J,Structural Mechanism for Statin Inhibition of HMG-CoA Reductase,Science 2001,292:1160-1164.
4.(a)Konoike T,Okada T and Araki Y,Optical Resolution of 3-(Silyloxy)glutaric Acid Half Esters and Their Utilization for Enantioconvergent Synthesis of a HMG-CoA Reductase Inhibitor,J.Org.Chem.1998,63,3037-3040;
(b)Wess G,Kesseler K,Baader E,Bartmann W,Beck G,Bergmann A,Jendralla H,Bock K,Holzstein O,Kleine H and Schnierer M,Stereoselective synthesis of HR 780 a new highly potent HMG-CoA reductase inhibitor,Tetrahedron Lett.1990,31:2545-2548;
(c)Konoike T and Araki Y,Practical Synthesis of Chiral Synthons for the Preparation of HMG-CoA Reductase Inhibitors,J.Org.Chem.1994,59:7849-7854;
(c)Brower PL,Butler DE,Deering CF,Le TV,Millar A,Nanninga TN and Roth BD,The synthesis of (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate,a key intermediate for the preparation of CI-981,a highly potent,tissue selective inhibitor of HMG-CoA reductase,Tetrahedron Lett.1992,33:2279-2282;
(d)Cho Y-H,Roh KR,Shin JH,Chun JP,Yu HS and Cho C-W,Process for producing optically pure β-hydroxy-ketoester derivatives,WO 2002096915,2002.
5.(a)Tempkin O,Abel S,Chen C-P,Underwood R,Prasad K,Chen K-M,Repic O and Blacklock T J,Asymmetric synthesis of 3,5-dihydroxy-6(E)-heptenoate-containing HMG-CoA reductase inhibitors,Tetrahedron 1997,53:10659-10670;
(b)Lynch JE,Volante RP,Wattley RV and Shinkai I,Synthesis of an HNG-CoA reductase inhibitor;a diastereoselective aldol approach,Tetrahedron Lett.1987,28:1385-1387;
(c)Beck G,Jendralla H and Kesseler K,Practical Large-Scale Synthesis of Tert-Butyl(3R,5S)-6-Hydroxy-3,5-O-Isopropylidene-3,5-Dihydroxyhexanoate:Essential Building-Block for Hmg-CoA Reductase Inhibitors,Synthesis 1995,1014-1018;
(d)Hiyama T,Minami T and Takahashi K,Synthesis of Artificial HMG-CoA Reductase Inhibitors Based on the Olefination Strategy,Bull.Chem.Soc.Jpn.1995,68:364-372;
(e)Minami T,Takahashi K and Hiyama T,Stereoselective reduction of β,δ-diketo esters derived from tartaric acid,Tetrahedron lett.1993,34:513-516;
(f)Urabe H,Matsuka T and Sato F,New Chiral Blocks for Introducing the Side Chain of HMG-CoA Reductase Inhibitors,Tetrahedron Lett.1992,33:4153-4156;
(g)Evans DA,Trenkle WC,Zhang J and Burch JD,Synthesis and Confirmation of the Absolute Stereochemistry of the(-)-Aflastatin A C_9-C_(27)Degradation Polyol,Org.Lett.2005,7:3335-3338;
(H)Evans DA,Kozlowski MC,Murry JA,Burgey CS,Campos KR,Connell BT and Staples RJ,C_2-Symmetdc Copper(Ⅱ)Complexes as Chiral Lewis Acids,J.Am.Chem.Soc.1999,121:669-685.
6.Chen K-M,Hardtmann GE,Prasad K,Repic O and Shapiro M J,1,3-syn-diastereoselective reduction of β-hydroxyketones utilizing alkoxydialkylboranes,Tetrahedron Lett.1987,28:155-158.
7.(a)Wolberg M,Hummel W,Wandrey C and Muller M,Highly regio-and enantioselective reduction of 3,5-dioxocarboxylate,Angew.Chem.Int.Ed.2000,39:4306-4307;
(b)Wolberg M,Hummel W and Muller M,Biocatalytic reduction of β,δ-diketo esters:a highly stereoselective approach to all four stereoisomers of a chlorinated β,δ-dihydroxy hexanoate,Chem.Eur.J.2001,7:4562-4571;
(c)Wolberg M,Kaluzna I.A,Muller M and Stewart JD,Regio and enantioselective reduction of t-butyl 6-chloro-3,5-dioxohexanoate with baker's yeast,Tetrahedron:Asymmetry 2004,15:2825-2828.
8.(a)Everaere K,Franceschini N,Mortreux A and Carpentier JF,Diastereoselective synthesis of syn-3,5-dihydroxyesters via ruthenium-catalyzed asymmetric transfer hydrogenation,Tetrahedron Lett.2002,43:2569-2571;
(b)Blandin V,Carpentier JF and Mortreux A,One-pot and sequential asymmetric hydrogenation of beta,delta-diketoesters into functionalized 1,3-diols:From anti-to syn-stereoselectivity,Eur.J.Org.Chem.1999,3421-3427.
9.(a)Patel RN,Banerjee A,McNamee CG,D Brzozowski,Hanson RL and Szarka L,Stereoselective microbial or enzymatic reduction of 3,5-dioxo esters to 3-hydroxy-5-oxo,3-oxo-5-hydroxy,and 3,5-dihydroxy esters,Enzyme Microb.Technol.1993,15:1014-1021;
(b)Guo Z,Chen Y,Goswami A,Hanson RL and Patel RN,Synthesis of ethyl and t-butyl (3R,5S)-dihydroxy-6-benzyloxy hexanoates via diastereo-and enantioselective microbial reduction,Tetrahedron:Asymmetry 2006,17:1589-1602.
10.(a)Tsujigami T,Sugai T and Ohta H,Microbial asymmetric reduction of α-hydroxy ketones in the anti-Preiog selectivity,Tetrahedron:Asymmetry 2001,12:2543-2549;
(b)Borah J.C,Gogoi S,Boruwa J,Kalita B and Barua NC,A highly efficient synthesis of the C-13 side-chain of taxol using Shibasaki's asymmetric Henry reaction,Tetrahedron Lett.2004,45:3689-3691.
11.Brandes A,Eggert U and Hoffmann HMR,Synthesis of Acyclic,Multifunctionalized α,α'-Disecondary Ethers with Full Control of Chemo-,Regio-and Enantioselectivity,Synlett 1994,745-747.
12.(a)House H,Czuba L.J,Gall M and Olmstend HD,Chemistry of carbonions.ⅩⅧ.Preparation of trimethylsilyl enol ethers,J.Org.Chem.1969,34:2324-2336;
(b)Olah GA,Gupta BGB,Narang SC and Malhotra R,Synthesis methods and reactions.71.Chlorotrimethylsilane and tert-butyl dimethylsilyi chloride/lithium sulfide,mild and efficient silylating reagents,J.Orig.Chem.1979,44:4272-4275.
13.(a)Shin HS,Choi BS,Lee KK,Chang JH,Lee KW,Nam DH and Kim N-S,Efficient Activation of Zinc:Application of the Blaise Reaction to an Expedient Synthesis of a Statin Intermediate,Synthesis 2004,2629-2632;
(b)Hannick SM and Kishi Y,An improved procedure for the Blaise reaction:a short,practical route to the key intermediates of the saxitoxin synthesis,J.Org.Chem.1983,48:3833-2835.
14.(a)Gerald C and Sandrine G-L,Selective hydrolysis of anti-1,3-diol-acetonides for the differentiation of 1,3-anti and 1,3-syn diols,Tetrahedron Lett.2006,47:671-674;
(b)Bode SE,Muller M and Wolherg M,Diastereomer-Differentiating Hydrolysis of 1,3-Diol-Acetonides:A Simplified Procedure for the Separation of syn-and anti-1,3-Diols,Org.Lett.2002,4:619-621.
15.(a)Partali V,Waagen V and Alivik T,Enzymic resolution of butanoic esters of 1-phenylmethyl and 1-(2-phenylethyl)ethers of 3-chloro-1,2-propanediol,Tetrahedron:Asymmetry 1993,4:961-968;
(b)Hansen TV,Waagen V,Partali V,Anthonsen HW and Anthonsen T,Cosolvent enhancement of enantioselectivity in lipase-catalyzed hydrolysis of racemic esters.A process for production of homochiral C-3 building blocks using iipase B from Candida antarctica,Tetrahedron:Asymmetry 1995,6:499-504;
(c)Pederson RL,Liu KK-C,Rutan JF,Chen L and Wong C-H,Enzymes in organic synthesis:synthesis of highly enantiomerically pure 1,2-epoxy aldehydes,epoxy alcohols,thiirane,aziridine,and glyceraldehyde 3-phosphate,J.Org.Chem.1990,55:4897-901;
(d)Lundhaug K,Overbeeke PLA,Jongejan JA and Anthonsen T,Organic co-solvents restore the inherently high enantiomeric ratio of lipase B from Candida antarctica in hydrolytic resolution by relieving the enantiospecific inhibition of product alcohol,Tetrahedron:Asymmetry 1998,9:2851-2856;
(e)Nakamura Y,Matsumoto T,Nomoto F,Ueda M,Fukuda H and Kondo A,Enhancement of Activity of Lipase-Displaying Yeast Cells and Their Application to Optical Resolution of (R,S)-1-Benzyloxy-3-Chloro-2-Propyl Monosuccinate,Biotechnol.Prog.2006,22:998-1002.
16.Sun F,Xu G,Wu J and Yang L,Efficient lipase-catalyzed kinetic resolution of 4-arylmethoxy-3-hydroxybutanenitriles:application to an expedient synthesis of a statin intermediate,Tetrahedron:Asymmetry 2006,17:2907-2913.
17.a)Naemura K,Murata M,Tanaka R,Yano M,Hirose K and Tobe Y,Enantioselective acylation of primary and secondary alcohols catalyzed by lipase QL from Alcaligenes sp:a predictive active site model for lipase QL to identify which enantiomer of an alcohol reacts faster in this acylation,Tetrahedron:Asymmetry 1996,7:3285-3294;
(b)Kim M-J and Choi YK,Lipase-catalyzed enantioselective transesterification of O-trityl 1,2-diols.Practical synthesis of (R)-tritylglycidol,J.Org.Chem.1992,57:165-1607.
18.Philips KD,Zemlicka J and Horwitz JP,Unsaturated sugars.1.Decarboxylative elimination of methyl 2,3-di-O-benzyl-a-D-glucopyranosiduronic acid to methyl 2,3-di-O-benzyl-4-deoxy -β-L-threo-pent-4-enopyranoside,Carbohydr.Res.1973,30:281-286.
19.(a)Haubenstock H and Eliel EL,Reductions with Metal Hydrides.Ⅺ.Solvent Effect on the Stereochemistry of Reduction with Sodium Borohydride,J.Am.Chem.Soc.1962,84:2368-2371;
(b)Cieplak AS,Stereochemistry of Nucleophilic Addition to Cyclohexanone.The Importance of Two-Electron Stabilizing InteractionsJ.Am.Chem.Soc.1981,103,4540-4552.
1.Graul A,Castaner J.Atorvastatin.Drugs Fut.,1997,22:956-965.
2.Istvan E S,Deisenhofer J.Structural mechanism for statin inhibition of HMG-CoA reductase.Science,2001,292:1160-1164.
3.Brower P L,Butler D E,Deering C F et al.The synthesis of(4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate,a key intermediate for the preparation of CI-981,a highly potent,tissue selective inhibitor of HMG-CoA reductase.Tetrahedron Lett.,1992,33(17):2279-2283.
4.Baumann K L,Butler D E,Deering C F et al.The convergent synthesis of CI-981,an optically active,highly potent,tissue selective inhibitor of HMG-CoA reductase.Tetrahedron Lett.,1992,33(17):2283-2284.
5.Butler D E,Le T V,Millar A.Process for the synthesis of(5R)-1,1-dimethylethyl-6-cyano-5-hydroxy-3-oxo-hexanoate.US5155251,1992.
6.Radi S.A new way to tert-butyl[(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]actetate,a key intermediate of atorvastatin synthesis.Synthetic Commun,2003,33(13):2275-2283.
7.Shin H S,Choi B S,Lee K K et al.Efficient activation of zinc:Application of the blaise reaction to an expedient synthesis of a statin intermediate.Synthesis,2004,16:2629-2632.
8.Beck G,Jendralla H,Kesseler K.Practical large-Scale synthesis of Tert-butyl(3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate:Essential building-block for HMG-CoA reductase inhibitors.Synthesis,1995,8:1014-1018.
9.Wolberg M,Hummel W,Muller M.Biocatalytic reduction of β,δ-diketo esters:A highly stereoselective approach to all four stereoisomers of a chlorinated β,δ-hihydroxy hexanote.Chem.Eur.J.,2001,7(21):4562-4571.
10.Zlicar M.Process for the synthesis of rosuvastatin calcium using L-malic acid for the side chain chirality.WO2007017117,2007.