降龙涎醚合成研究进展
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摘要
降龙涎醚具有特殊的龙涎香香气,因其独特的香气特征和特有的定香能力被广泛应用于各种香精配方。目前降龙涎醚的工业生产主要以香紫苏醇、β-二氢紫罗兰酮、金合欢醇类似物为原料进行制备,但这些生产方法从绿色化学的角度来看依然存在诸多的问题。综述了降龙涎醚合成的研究进展,详细阐述了以香紫苏醇为起始原料的合成方法研究进展。其中,以香紫苏醇为起始原料,双氧水作为氧化剂,通过杂多酸盐等催化剂催化合成降龙涎醚,操作简便,污染小,是极具潜力的绿色合成方法。
(-)-Ambrox has been recognized as the prototype of all ambergris odorants and used as a valuable ingredient in various flavor and fragrance formulations, because of its unique scent and scent fixative function. In current commercial synthesis processes of(-)-Ambrox, major starting raw materials include sclareol, β-dihydroionone and homofarnesol. All these chemical routes have many problems in terms of green chemistry. This review summarized recent progress in Ambrox synthesis and especially expounded progress with sclareol. Among them, one-pot synthesis using sclareol and hydrogen peroxide in the presence of polyoxometalates catalyst has advantages of easy operation and low pollution, which is a potential green synthetic technique.
(-)-Ambrox has been recognized as the prototype of all ambergris odorants and used as a valuable ingredient in various flavor and fragrance formulations, because of its unique scent and scent fixative function. In current commercial synthesis processes of(-)-Ambrox, major starting raw materials include sclareol, β-dihydroionone and homofarnesol. All these chemical routes have many problems in terms of green chemistry. This review summarized recent progress in Ambrox synthesis and especially expounded progress with sclareol. Among them, one-pot synthesis using sclareol and hydrogen peroxide in the presence of polyoxometalates catalyst has advantages of easy operation and low pollution, which is a potential green synthetic technique.
引文
[1]MARTINEZ-GUIDO S I,GONZALEZ-CAMPOS J B,DEL-RIO R E,et al.A multiobjective optimization approach for the development of a sustainable supply chain of a new fixative in the perfume industry[J].ACS Sustainable Chemistry&Engineering,2014,2(10):2380-2390.
[2]CHAUFFAT C,MORRIS A.From ambergris to Cetalox laevo tradition,innovation and creation[J].Perfumer&Flavorist,2004,29:34-41.
[3]ESCHER S,GIERSCH W,NICLASS Y,et al.Configuration-odor relationships in 5β-ambrox[J].Helvetica Chimica Acta,1990,73(9):1935-1947.
[4]黄明泉,孙宝国,田红玉,等.龙涎香分子结构与香气关系规律研究进展[C]//2006年中国香料香精学术研讨会论文集.2006:20-25.HUANG M Q,SUN B G,TIAN H Y,et al.The development of research in the relationships between ambergris and molecular structure[C]//Proceedings of the Symposium on Chinese Flavor and Fragrance in 2006.2006:20-25.
[5]王文军,陈莎,戴乾圜.龙涎香的组成及降龙涎醚的合成研究进展[J].有机化学,2001,21(3):167-172.WANG W J,CHEN S,DAI Q H.The composition of ambergris and the development of the synthesis of(-)-Ambrox[J].Chinese Journal of Organic Chemistry,2001,21(3):167-172.
[6]陆佳庆,潘仙华,欧文华,等.降龙涎香醚的合成进展[J].香料香精化妆品,2008,44(2):23-30.LU J Q,PANG X H,OU W H,et al.Study on synthesis evolution of Ambrox[J].Flavour Fragance Cosmetics,2008,44(2):23-30.
[7]GB2760—2011.食品安全国家标准食品添加剂使用标准[S].北京:中国标准出版社,2011.GB2760—2011.National food safety standard-standards for uses of food additives[S].Beijing:Standards Press of China,2011.
[8]LEFFINGWELL J,LEFFINGWELL D.Chiral chemistry in flavours&fragrances[J].Speciality Chemicals Magazine,2011,3:30-33.
[9]STOLL M,HINDER M.Odeur et Constitution(Ⅲ):Les substances bicyclohomofarnésiques[J].Helvetica Chimica Acta,1950,33(5):1251-1260.
[10]KAWANOBE T,KOGAMI K,MATSUI M.New syntheses of(±)-Ambrox,(+)-Ambra oxide and their stereoisomers[J].Agricultural and Biological Chemistry,1986,50(6):1475-1480.
[11]SNOWDEN R L,EICHENBERGER J C,LINDER S M,et al.Internal nucleophilic termination in biomimetic acid mediated polyene cyclizations:stereochemical and mechanistic implications.Synthesis of(±)-Ambrox and its diastereoisomers[J].Journal of Organic Chemistry,1992,57(3):955-960.
[12]SUNISA S,SURACHAI P,NONGNUJ M.Synthesis of ent-ambrox from(-)-nidorellol[J].Tetrahedron Letters,2012,53(40):5418-5421.
[13]CHARLES F,IRIS M,LIOEL S,et al.Trans-tetrahydrofurans by OH-assisted Ru-catalyzed isomerization of 2-butene-1,4-diols[J].European Journal of Organic Chemistry,2010,2010(32):6153-6156.
[14]ROSALES A,FOLEY L A R,PADIAL N M,et al.Diastereoselective synthesis of(±)-Ambrox by titanium(Ⅲ)-catalyzed radical tandem cyclization[J].Synlett,2016,27(3):369-374.
[15]FONTANEDA R,ALONSO P,FANANAS F J,et al.Scalable synthesis of the amber odorant 9-epi-Ambrox through a biomimetic cationic cyclization/nucleophilic bromination reaction[J].Organic Letters,2016,18(18):4626-4629.
[16]MA M,FENG J,LI R,et al.Synthesis and antifungal activity of ethers,alcohols,and iodohydrin derivatives of sclareol against phytopathogenic fungi in vitro[J].Bioorganic&Medicinal Chemistry Letters,2015,25(14):2773-2777.
[17]CHAPUIS C.Enantioselective access to(-)-Ambrox?starting fromβ-farnesene[J].Helvetica Chimica Acta,2014,97(2):197-214.
[18]SEITZ M,SYREN P O,STEINER L,et al.Synthesis of heterocyclic terpenoids by promiscuous squalene-hopene cyclases[J].Chem Bio Chem,2013,14(4):436-439.
[19]XIE Y P,LI B G,LUO Y G,et al.Preparation of two diastereoisomeric decalin synthons and(-)-Ambrox[J].Helvetica Chimica Acta,2008,91(4):734-740.
[20]SHEN Y C,CHENG S Y,KUO Y H,et al.Chemical transformation and biological activities of ambrein,a major product of ambergris from Physeter macrocephalus(Sperm Whale)[J].Journal of Natural Products,2007,70(2):147-153.
[21]ALONSO P,PARDO P,FONTANEDA R,et al.Synthesis and applications of cyclohexenyl halides obtained by a cationic carbocyclisation reaction[J].Chemistry-A European Journal,2017,23(53):13158-13163.
[22]EICHHORN E,SCHILLING B,WAHLER D,et al.Squalene-hopene cyclase variants for the preparation of Ambrox from homofarnesol with purification of Ambrox for cosmetic use:WO2016170099A1[P].2016.
[23]EICHHORN E.Manufacture of Ambrox from homofarnesol with purification of Ambrox for cosmetic use:WO2016170106A1[P].2016.
[24]KOYAMA H,KAKU Y,OHNO M.Synthesis of(–)-Ambrox from?-abietic acid[J].Tetrahedron Letters,1987,28(25):2863-2866.
[25]BARRERO A F,ALTAREJOS J,ALVAREZ-MANZANEDA E J,et al.Synthesis of Ambrox?from communic acids[J].Tetrahedron,1993,49(28):6251-6262.
[26]BARRERO A F,ALVAREZ-MANZANEDA E J,ALTAREJOS J,et al.Synthesis of Ambrox?from(-)-sclareol and(+)-cis-abienol[J].Tetrahedron,1993,49(45):10405-10412.
[27]VERSTEGEN-HAAKSMA A A,SWARTS H J,JANSEN B J,et al.Total synthesis of(-)-Ambrox?from S-(+)-carvone(part 6)[J].Tetrahedron,1994,50(33):10095-10106.
[28]BARRERO A F,ALTAREJOS J,ALVAREZ-MANZANEDA E J,et al.Synthesis of(±)-Ambrox from(E)-nerolidol andβ-ionone via allylic alcohol[2,3]sigmatropic rearrangement[J].Journal of Organic Chemistry,1996,61(6):2215-2218.
[29]BOLSTER M G,JANSEN B J M,DE-GROOT A.The synthesis of(-)-Ambrox?starting from labdanolic acid[J].Tetrahedron,2001,57(26):5657-5662.
[30]CASTRO J M,SALIDO S,ALTAREJOS J,et al.Synthesis of Ambrox?from labdanolic acid[J].Tetrahedron,2002,58(29):5941-5949.
[31]ISHIHARA K,ISHIBASHI H,YAMAMOTO H.Enantio-and diastereoselective stepwise cyclization of polyprenoids induced by chiral and achiral LBAs.A new entry to(-)-Ambrox,(+)-Podocarpa-8,11,13-triene Diterpenoids,and(-)-Tetracyclic polyprenoid of sedimentary origin[J].Journal of the American Chemical Society,2002,124(14):3647-3655.
[32]YANG H J,LI B G,CAI X H,et al.Chiral decalins:preparation from oleanolic acid and application in the synthesis of(-)-9-epi-Ambrox[J].Journal of Natural Products,2006,69(11):1531-1538.
[33]SUWANCHAROEN S,PORNPAKAKUL S,MUANMSIN N.Synthesis of ent-Ambrox?from(-)-nidorellol[J].Tetrahedron Letters,2012,53(40):5418-5421.
[34]EVANS G B,CAMERON S A,CULBERT S R,et al.Convenient syntheses of ring-B-nor analogues of Ambrox?and amberketal via a novel ring contraction reaction[J].Tetrahedron Letters,2014,55(45):6227-6230.
[35]白杨.柠檬醛合成龙涎香型香料工艺研究[D].北京:北京林业大学,2009.BAI Y.Study on synthesis technology of ambergris-like perfume from citral[D].Beijing:Beijing Forestry University,2009.
[36]吴亚.香紫苏醇氧化降解合成香紫苏内酯的研究[D].西安:陕西师范大学,2005.WU Y.Oxidative degradation of sclareoi into sclareolide by hydrogen peroxide[D].Xi’an:Shaanxi Normal University,2005.
[37]BARRERO A F,ALVAREZ-MANZANEDA E J,CHAHBOUN R,et al.Degradation of the side chain of(-)-sclareol:a very short synthesis of nor-Ambreinolide and Ambrox[J].Synthetic Communications,2004,34(19):3631-3643.
[38]HENLEY W M,JOSEPH N S,TEAGUE J C.Two stage oxidation of sclareol:US3050532[P].1962.
[39]OGURA T,MATSUOKA H,YAMANAKA T.L-ambrox:JP6133184[P].1984.
[40]李丽慧,吕艳羽,杨绍祥,等.高锰酸钾用量对制备香紫苏内酯和降龙涎二醇的影响[J].日用化学工业,2015,45(2):107-109.LI L H,LüY Y,YANG S X,et al.Influence of potassium permanganate dosage on preparation of sclareolide and ambradiol[J].China Surfactant Detergent&Cosmetics,2015,45(2):107-109.
[41]翟周平.香紫苏内酯合成新工艺的研究[J].香料香精化妆品,2002,38(6):1-2+40.ZHAI Z P.The new technology for synthesis of sclareolid[J].Flavour Fragance Cosmetics,2002,38(6):1-2+40.
[42]吕艳羽,李丽慧,刘永国,等.高锰酸钾氧化法制备香紫苏内酯反应固体废弃物的分析[J].化学试剂,2014,36(10):913-915.LüY Y,LI L H,LIU Y G,et al.Solid waste analysis for preparation of sclareolide reaction via potassium permanganate oxidation[J].Chemical Regents,2014,36(10):913-915.
[43]杨绍祥,郝颜峰,李丽慧,等.高锰酸钾氧化法制备香紫苏内酯反应废水的有效处理[J].化学试剂,2016,38(3):236-238+258.YANG S X,HAO Y F,LI L H,et al.Effluent effective treatment for preparation of sclareolide reaction via potassium permanganate oxidation[J].Chemical Reagents,2016,38(3):236-238+258.
[44]王文军,戴乾圜,陈莎.香紫苏醇侧链的氧化降解[J].有机化学,2003,23(1):95-99.WANG W J,DAI Q H,CHEN S.Oxidation and degradation of the sclareol side chain[J].Chinese Journal of Organic Chemistry,2003,23(3):95-99.
[45]BARTON D H R,PAREKH S I,TAYLOR D K,et al.An efficient synthesis of(-)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan from(-)-sclareol[J].Tetrahedron Letters,1994,35(32):5801-5804.
[46]MARTRES P,PERFETTI P,ZAHRA J P,et al.A short and efficient syntheis of(-)-ambrox from(-)-sclareol using a rutheniumoxide catalyzed key step[J].Tetrahedron Letters,1993,34(4):629-632.
[47]MARTRES P,PERFETTI P,ZAHRA J P,et al.A short efficient synthesis of ambraketal and epiambraketal from sclareol[J].Tetrahedron Letters,1994,35(1):97-98.
[48]RENE D,FERDINAND N,GEORGE M W.Novel hydroperoxide and use of same as intermediate for the preparation of 3α,6,6,9α-tatram ethylperhydromaphtho(2,1-b)furan:US4734530[P].1998.
[49]魏俊发,吴亚,石先莹,等,香紫苏内酯的合成方法:1683352A[P].2005.WEI J F,WU Y,SHI X Y,et al.Sclareolide synthetic method with low cost:1683352A[P].2005.
[50]翟周平,胡新予,赵新春,等.四丁基溴化铵催化过氧化氢氧化香紫苏醇合成香紫苏内酯的研究[J].香料香精化妆品,2009,45(4):1-3.ZHAI Z P,HU X Y,ZHAO X C,et al.Catalytic synthesis of sclareolide with tetrabutylammonium bromide as catalyst and hydrogen peroxide as oxidant[J].Flavour Fragance Cosmetics,2008,44(4):23-30.
[51]MOULINES J,BATS J P,LAMIDEY A M,et al.About a practical synthesis of Ambrox?from sclareol:a new preparation of a ketone key intermediate and a close look at its Baeyer-Villiger oxidation[J].Helvetica Chimica Acta,2004,87(10):2695-2705.
[52]YANG L,WILLIAMS D E,MUI A,et al.Synthesis of pelorol and analogues:activators of the inositol 5-phosphatase Ship[J].Organic Letters,2005,7(6):1073-1076.
[53]郝颜峰,杨绍祥,李丽慧,等.降龙涎二醇的合成工艺研究[J].日用化学工业,2016,46(2):111-113.HAO Y F,YANG S X,LI L H,et al.Synthesis of ambradiol[J].China Surfactant Detergent&Cosmetics,2016,46(2):111-113.
[54]ALVAREZ-MANZANEDA E J,CHABOUN R,ALVAREZ E,et al.Cerium(Ⅳ)ammonium nitrate(CAN):a very efficient reagent for the synthesis of tertiary ethers[J].Synlett,2006,(12):1829-1834.
[55]JULIEN B N,PARK G E,BURLINGAME R.Recombinant microorganism producing sclareol synthase and labdenediol diphosphate synthase for ambroxide synthesis:WO2014022434[P].2014.
[56]NUNES F M N,IMAMURA P M.A convenient preparation of ambergris odorants from copalic acid[J].Journal of the Brazilian Chemical Society,1996,7(3):181-186.
[57]ARICO F,TUNDO P,MARANZANA A,et al.Synthesis of five-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate[J].Chem Sus Chem,2012,5(8):1578-1586.
[58]ARICO F,TUNDO P.Five-membered N-and O-heterocycles by dimethyl carbonate chemistry[J].Green Syntheses Series,2014,1:205-218.
[59]ISHII Y,YAMAWAKI K,URA T,et al.Hydrogen peroxide oxidation catalyzed by heteropoly acids combined with cetylpyridinium chloride.Epoxidation of olefins and allylic alcohols,ketonization of alcohols and diols,and oxidative cleavage of 1,2-diols and olefins[J].Journal of Organic Chemistry,1988,53(15):3587-3593.
[60]陶飞燕,杨绍祥,杨文敏,等.一种降龙涎香醚的制备方法:105017191 B[P].2015.TAO F Y,YANG S X,YANG W M,et al.A method for preparing Ambrox:105017191 B[P].2015.
[61]陶飞燕,杨绍祥,杨文敏,等.一种制备降龙涎香醚的方法:105037308 B[P].2015.TAO F Y,YANG S X,YANG W M,et al.A method for preparing Ambrox:105037308 B[P].2015.
[62]DECORZANT R,VIAL C,NAF F.A short synthesis of Ambrox?from sclareol[J].Tetrahedron,1987,43(8):1871-1879.
[63]PHILIP A C.Synthesis of dodecahydro-3a,6,6,9a-tetramethyl naphtho[2,1-b]furan via alkoxy radical fragmentation[J].Tetrahedron,1988,44(7):1925-1932.
[64]YANG S X,TIAN H Y,SUN B G,et al.One-pot synthesis of(-)-Ambrox[J].Scientific Reports,2016,6:32650.
[65]FARBOOD M I,MORRIS J A,DOWNEY A E.Process for producing a cyclic ether:US5155029[P].1992.
[66]LAVILLE R,CASTEL C,FATTARSI K,et al.Low sclareol by-product of clary sage concrete:chemical analysis of a waste product of the perfume industry[J].Flavour and Fragrance Journal,2013,28(2):93-101.
[67]SCHALK M,PASTORE L,MIRATA M A,et al.Toward a biosynthetic route to sclareol and amber odorants[J].Journal of the American Chemical Society,2012,134(46):18900-18903.
[68]MARTINS M P,OUAZZANI J,ARCILE G,et al.Biohydroxylation of(-)-Ambrox,(-)-sclareol,and(+)-sclareolide by whole cells of Brazilian marine-derived fungi[J].Marine Biotechnology,2015,17(2):211-218.
[69]MARTINEZ-GUIDO S I,SENGUPTA D,NAPOLES-RIVERA F,et al.Life cycle assessment for Ambrox production from different chemical routes[J].Journal of Cleaner Production,2016,130(1):202-212.
[70]SCHALK M,ROCCI L.Fermentative production of(+)-manool by recombinant Escherichia coli expressing copalyl diphosphate synthase and sclareol synthase genes:WO2017001641A1[P].2017.
[71]BREUER M,SIEGEL W,RUEDENAUER S,et al.Enzymatic cyclization of homofarnesylic acid by a heterologous squalene-hopene cyclase expressed in Escherichia coli:WO2017140909A1[P].2017.
[72]DEL RIO TORRES R E N,GOMEZ HURTADO M A,PEREZ GUTIERREZ A I,et al.Method for synthesizing ambroxide from 13,14,15,16-tetranor-8α,12-labdanediol:WO2017068400A1[P].2017.
[73]DEL RIO TORRES R E N,GOMEZ HURTADO M A,PEREZ GUTIERREZ A I,et al.Method for synthesizing ambroxide from Ageratina jocotepecana via(-)-13,14,15,16-tetranor-8α,12-labdanediol:WO2017068401A1[P].2017.
[2]CHAUFFAT C,MORRIS A.From ambergris to Cetalox laevo tradition,innovation and creation[J].Perfumer&Flavorist,2004,29:34-41.
[3]ESCHER S,GIERSCH W,NICLASS Y,et al.Configuration-odor relationships in 5β-ambrox[J].Helvetica Chimica Acta,1990,73(9):1935-1947.
[4]黄明泉,孙宝国,田红玉,等.龙涎香分子结构与香气关系规律研究进展[C]//2006年中国香料香精学术研讨会论文集.2006:20-25.HUANG M Q,SUN B G,TIAN H Y,et al.The development of research in the relationships between ambergris and molecular structure[C]//Proceedings of the Symposium on Chinese Flavor and Fragrance in 2006.2006:20-25.
[5]王文军,陈莎,戴乾圜.龙涎香的组成及降龙涎醚的合成研究进展[J].有机化学,2001,21(3):167-172.WANG W J,CHEN S,DAI Q H.The composition of ambergris and the development of the synthesis of(-)-Ambrox[J].Chinese Journal of Organic Chemistry,2001,21(3):167-172.
[6]陆佳庆,潘仙华,欧文华,等.降龙涎香醚的合成进展[J].香料香精化妆品,2008,44(2):23-30.LU J Q,PANG X H,OU W H,et al.Study on synthesis evolution of Ambrox[J].Flavour Fragance Cosmetics,2008,44(2):23-30.
[7]GB2760—2011.食品安全国家标准食品添加剂使用标准[S].北京:中国标准出版社,2011.GB2760—2011.National food safety standard-standards for uses of food additives[S].Beijing:Standards Press of China,2011.
[8]LEFFINGWELL J,LEFFINGWELL D.Chiral chemistry in flavours&fragrances[J].Speciality Chemicals Magazine,2011,3:30-33.
[9]STOLL M,HINDER M.Odeur et Constitution(Ⅲ):Les substances bicyclohomofarnésiques[J].Helvetica Chimica Acta,1950,33(5):1251-1260.
[10]KAWANOBE T,KOGAMI K,MATSUI M.New syntheses of(±)-Ambrox,(+)-Ambra oxide and their stereoisomers[J].Agricultural and Biological Chemistry,1986,50(6):1475-1480.
[11]SNOWDEN R L,EICHENBERGER J C,LINDER S M,et al.Internal nucleophilic termination in biomimetic acid mediated polyene cyclizations:stereochemical and mechanistic implications.Synthesis of(±)-Ambrox and its diastereoisomers[J].Journal of Organic Chemistry,1992,57(3):955-960.
[12]SUNISA S,SURACHAI P,NONGNUJ M.Synthesis of ent-ambrox from(-)-nidorellol[J].Tetrahedron Letters,2012,53(40):5418-5421.
[13]CHARLES F,IRIS M,LIOEL S,et al.Trans-tetrahydrofurans by OH-assisted Ru-catalyzed isomerization of 2-butene-1,4-diols[J].European Journal of Organic Chemistry,2010,2010(32):6153-6156.
[14]ROSALES A,FOLEY L A R,PADIAL N M,et al.Diastereoselective synthesis of(±)-Ambrox by titanium(Ⅲ)-catalyzed radical tandem cyclization[J].Synlett,2016,27(3):369-374.
[15]FONTANEDA R,ALONSO P,FANANAS F J,et al.Scalable synthesis of the amber odorant 9-epi-Ambrox through a biomimetic cationic cyclization/nucleophilic bromination reaction[J].Organic Letters,2016,18(18):4626-4629.
[16]MA M,FENG J,LI R,et al.Synthesis and antifungal activity of ethers,alcohols,and iodohydrin derivatives of sclareol against phytopathogenic fungi in vitro[J].Bioorganic&Medicinal Chemistry Letters,2015,25(14):2773-2777.
[17]CHAPUIS C.Enantioselective access to(-)-Ambrox?starting fromβ-farnesene[J].Helvetica Chimica Acta,2014,97(2):197-214.
[18]SEITZ M,SYREN P O,STEINER L,et al.Synthesis of heterocyclic terpenoids by promiscuous squalene-hopene cyclases[J].Chem Bio Chem,2013,14(4):436-439.
[19]XIE Y P,LI B G,LUO Y G,et al.Preparation of two diastereoisomeric decalin synthons and(-)-Ambrox[J].Helvetica Chimica Acta,2008,91(4):734-740.
[20]SHEN Y C,CHENG S Y,KUO Y H,et al.Chemical transformation and biological activities of ambrein,a major product of ambergris from Physeter macrocephalus(Sperm Whale)[J].Journal of Natural Products,2007,70(2):147-153.
[21]ALONSO P,PARDO P,FONTANEDA R,et al.Synthesis and applications of cyclohexenyl halides obtained by a cationic carbocyclisation reaction[J].Chemistry-A European Journal,2017,23(53):13158-13163.
[22]EICHHORN E,SCHILLING B,WAHLER D,et al.Squalene-hopene cyclase variants for the preparation of Ambrox from homofarnesol with purification of Ambrox for cosmetic use:WO2016170099A1[P].2016.
[23]EICHHORN E.Manufacture of Ambrox from homofarnesol with purification of Ambrox for cosmetic use:WO2016170106A1[P].2016.
[24]KOYAMA H,KAKU Y,OHNO M.Synthesis of(–)-Ambrox from?-abietic acid[J].Tetrahedron Letters,1987,28(25):2863-2866.
[25]BARRERO A F,ALTAREJOS J,ALVAREZ-MANZANEDA E J,et al.Synthesis of Ambrox?from communic acids[J].Tetrahedron,1993,49(28):6251-6262.
[26]BARRERO A F,ALVAREZ-MANZANEDA E J,ALTAREJOS J,et al.Synthesis of Ambrox?from(-)-sclareol and(+)-cis-abienol[J].Tetrahedron,1993,49(45):10405-10412.
[27]VERSTEGEN-HAAKSMA A A,SWARTS H J,JANSEN B J,et al.Total synthesis of(-)-Ambrox?from S-(+)-carvone(part 6)[J].Tetrahedron,1994,50(33):10095-10106.
[28]BARRERO A F,ALTAREJOS J,ALVAREZ-MANZANEDA E J,et al.Synthesis of(±)-Ambrox from(E)-nerolidol andβ-ionone via allylic alcohol[2,3]sigmatropic rearrangement[J].Journal of Organic Chemistry,1996,61(6):2215-2218.
[29]BOLSTER M G,JANSEN B J M,DE-GROOT A.The synthesis of(-)-Ambrox?starting from labdanolic acid[J].Tetrahedron,2001,57(26):5657-5662.
[30]CASTRO J M,SALIDO S,ALTAREJOS J,et al.Synthesis of Ambrox?from labdanolic acid[J].Tetrahedron,2002,58(29):5941-5949.
[31]ISHIHARA K,ISHIBASHI H,YAMAMOTO H.Enantio-and diastereoselective stepwise cyclization of polyprenoids induced by chiral and achiral LBAs.A new entry to(-)-Ambrox,(+)-Podocarpa-8,11,13-triene Diterpenoids,and(-)-Tetracyclic polyprenoid of sedimentary origin[J].Journal of the American Chemical Society,2002,124(14):3647-3655.
[32]YANG H J,LI B G,CAI X H,et al.Chiral decalins:preparation from oleanolic acid and application in the synthesis of(-)-9-epi-Ambrox[J].Journal of Natural Products,2006,69(11):1531-1538.
[33]SUWANCHAROEN S,PORNPAKAKUL S,MUANMSIN N.Synthesis of ent-Ambrox?from(-)-nidorellol[J].Tetrahedron Letters,2012,53(40):5418-5421.
[34]EVANS G B,CAMERON S A,CULBERT S R,et al.Convenient syntheses of ring-B-nor analogues of Ambrox?and amberketal via a novel ring contraction reaction[J].Tetrahedron Letters,2014,55(45):6227-6230.
[35]白杨.柠檬醛合成龙涎香型香料工艺研究[D].北京:北京林业大学,2009.BAI Y.Study on synthesis technology of ambergris-like perfume from citral[D].Beijing:Beijing Forestry University,2009.
[36]吴亚.香紫苏醇氧化降解合成香紫苏内酯的研究[D].西安:陕西师范大学,2005.WU Y.Oxidative degradation of sclareoi into sclareolide by hydrogen peroxide[D].Xi’an:Shaanxi Normal University,2005.
[37]BARRERO A F,ALVAREZ-MANZANEDA E J,CHAHBOUN R,et al.Degradation of the side chain of(-)-sclareol:a very short synthesis of nor-Ambreinolide and Ambrox[J].Synthetic Communications,2004,34(19):3631-3643.
[38]HENLEY W M,JOSEPH N S,TEAGUE J C.Two stage oxidation of sclareol:US3050532[P].1962.
[39]OGURA T,MATSUOKA H,YAMANAKA T.L-ambrox:JP6133184[P].1984.
[40]李丽慧,吕艳羽,杨绍祥,等.高锰酸钾用量对制备香紫苏内酯和降龙涎二醇的影响[J].日用化学工业,2015,45(2):107-109.LI L H,LüY Y,YANG S X,et al.Influence of potassium permanganate dosage on preparation of sclareolide and ambradiol[J].China Surfactant Detergent&Cosmetics,2015,45(2):107-109.
[41]翟周平.香紫苏内酯合成新工艺的研究[J].香料香精化妆品,2002,38(6):1-2+40.ZHAI Z P.The new technology for synthesis of sclareolid[J].Flavour Fragance Cosmetics,2002,38(6):1-2+40.
[42]吕艳羽,李丽慧,刘永国,等.高锰酸钾氧化法制备香紫苏内酯反应固体废弃物的分析[J].化学试剂,2014,36(10):913-915.LüY Y,LI L H,LIU Y G,et al.Solid waste analysis for preparation of sclareolide reaction via potassium permanganate oxidation[J].Chemical Regents,2014,36(10):913-915.
[43]杨绍祥,郝颜峰,李丽慧,等.高锰酸钾氧化法制备香紫苏内酯反应废水的有效处理[J].化学试剂,2016,38(3):236-238+258.YANG S X,HAO Y F,LI L H,et al.Effluent effective treatment for preparation of sclareolide reaction via potassium permanganate oxidation[J].Chemical Reagents,2016,38(3):236-238+258.
[44]王文军,戴乾圜,陈莎.香紫苏醇侧链的氧化降解[J].有机化学,2003,23(1):95-99.WANG W J,DAI Q H,CHEN S.Oxidation and degradation of the sclareol side chain[J].Chinese Journal of Organic Chemistry,2003,23(3):95-99.
[45]BARTON D H R,PAREKH S I,TAYLOR D K,et al.An efficient synthesis of(-)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan from(-)-sclareol[J].Tetrahedron Letters,1994,35(32):5801-5804.
[46]MARTRES P,PERFETTI P,ZAHRA J P,et al.A short and efficient syntheis of(-)-ambrox from(-)-sclareol using a rutheniumoxide catalyzed key step[J].Tetrahedron Letters,1993,34(4):629-632.
[47]MARTRES P,PERFETTI P,ZAHRA J P,et al.A short efficient synthesis of ambraketal and epiambraketal from sclareol[J].Tetrahedron Letters,1994,35(1):97-98.
[48]RENE D,FERDINAND N,GEORGE M W.Novel hydroperoxide and use of same as intermediate for the preparation of 3α,6,6,9α-tatram ethylperhydromaphtho(2,1-b)furan:US4734530[P].1998.
[49]魏俊发,吴亚,石先莹,等,香紫苏内酯的合成方法:1683352A[P].2005.WEI J F,WU Y,SHI X Y,et al.Sclareolide synthetic method with low cost:1683352A[P].2005.
[50]翟周平,胡新予,赵新春,等.四丁基溴化铵催化过氧化氢氧化香紫苏醇合成香紫苏内酯的研究[J].香料香精化妆品,2009,45(4):1-3.ZHAI Z P,HU X Y,ZHAO X C,et al.Catalytic synthesis of sclareolide with tetrabutylammonium bromide as catalyst and hydrogen peroxide as oxidant[J].Flavour Fragance Cosmetics,2008,44(4):23-30.
[51]MOULINES J,BATS J P,LAMIDEY A M,et al.About a practical synthesis of Ambrox?from sclareol:a new preparation of a ketone key intermediate and a close look at its Baeyer-Villiger oxidation[J].Helvetica Chimica Acta,2004,87(10):2695-2705.
[52]YANG L,WILLIAMS D E,MUI A,et al.Synthesis of pelorol and analogues:activators of the inositol 5-phosphatase Ship[J].Organic Letters,2005,7(6):1073-1076.
[53]郝颜峰,杨绍祥,李丽慧,等.降龙涎二醇的合成工艺研究[J].日用化学工业,2016,46(2):111-113.HAO Y F,YANG S X,LI L H,et al.Synthesis of ambradiol[J].China Surfactant Detergent&Cosmetics,2016,46(2):111-113.
[54]ALVAREZ-MANZANEDA E J,CHABOUN R,ALVAREZ E,et al.Cerium(Ⅳ)ammonium nitrate(CAN):a very efficient reagent for the synthesis of tertiary ethers[J].Synlett,2006,(12):1829-1834.
[55]JULIEN B N,PARK G E,BURLINGAME R.Recombinant microorganism producing sclareol synthase and labdenediol diphosphate synthase for ambroxide synthesis:WO2014022434[P].2014.
[56]NUNES F M N,IMAMURA P M.A convenient preparation of ambergris odorants from copalic acid[J].Journal of the Brazilian Chemical Society,1996,7(3):181-186.
[57]ARICO F,TUNDO P,MARANZANA A,et al.Synthesis of five-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate[J].Chem Sus Chem,2012,5(8):1578-1586.
[58]ARICO F,TUNDO P.Five-membered N-and O-heterocycles by dimethyl carbonate chemistry[J].Green Syntheses Series,2014,1:205-218.
[59]ISHII Y,YAMAWAKI K,URA T,et al.Hydrogen peroxide oxidation catalyzed by heteropoly acids combined with cetylpyridinium chloride.Epoxidation of olefins and allylic alcohols,ketonization of alcohols and diols,and oxidative cleavage of 1,2-diols and olefins[J].Journal of Organic Chemistry,1988,53(15):3587-3593.
[60]陶飞燕,杨绍祥,杨文敏,等.一种降龙涎香醚的制备方法:105017191 B[P].2015.TAO F Y,YANG S X,YANG W M,et al.A method for preparing Ambrox:105017191 B[P].2015.
[61]陶飞燕,杨绍祥,杨文敏,等.一种制备降龙涎香醚的方法:105037308 B[P].2015.TAO F Y,YANG S X,YANG W M,et al.A method for preparing Ambrox:105037308 B[P].2015.
[62]DECORZANT R,VIAL C,NAF F.A short synthesis of Ambrox?from sclareol[J].Tetrahedron,1987,43(8):1871-1879.
[63]PHILIP A C.Synthesis of dodecahydro-3a,6,6,9a-tetramethyl naphtho[2,1-b]furan via alkoxy radical fragmentation[J].Tetrahedron,1988,44(7):1925-1932.
[64]YANG S X,TIAN H Y,SUN B G,et al.One-pot synthesis of(-)-Ambrox[J].Scientific Reports,2016,6:32650.
[65]FARBOOD M I,MORRIS J A,DOWNEY A E.Process for producing a cyclic ether:US5155029[P].1992.
[66]LAVILLE R,CASTEL C,FATTARSI K,et al.Low sclareol by-product of clary sage concrete:chemical analysis of a waste product of the perfume industry[J].Flavour and Fragrance Journal,2013,28(2):93-101.
[67]SCHALK M,PASTORE L,MIRATA M A,et al.Toward a biosynthetic route to sclareol and amber odorants[J].Journal of the American Chemical Society,2012,134(46):18900-18903.
[68]MARTINS M P,OUAZZANI J,ARCILE G,et al.Biohydroxylation of(-)-Ambrox,(-)-sclareol,and(+)-sclareolide by whole cells of Brazilian marine-derived fungi[J].Marine Biotechnology,2015,17(2):211-218.
[69]MARTINEZ-GUIDO S I,SENGUPTA D,NAPOLES-RIVERA F,et al.Life cycle assessment for Ambrox production from different chemical routes[J].Journal of Cleaner Production,2016,130(1):202-212.
[70]SCHALK M,ROCCI L.Fermentative production of(+)-manool by recombinant Escherichia coli expressing copalyl diphosphate synthase and sclareol synthase genes:WO2017001641A1[P].2017.
[71]BREUER M,SIEGEL W,RUEDENAUER S,et al.Enzymatic cyclization of homofarnesylic acid by a heterologous squalene-hopene cyclase expressed in Escherichia coli:WO2017140909A1[P].2017.
[72]DEL RIO TORRES R E N,GOMEZ HURTADO M A,PEREZ GUTIERREZ A I,et al.Method for synthesizing ambroxide from 13,14,15,16-tetranor-8α,12-labdanediol:WO2017068400A1[P].2017.
[73]DEL RIO TORRES R E N,GOMEZ HURTADO M A,PEREZ GUTIERREZ A I,et al.Method for synthesizing ambroxide from Ageratina jocotepecana via(-)-13,14,15,16-tetranor-8α,12-labdanediol:WO2017068401A1[P].2017.