天然产物Sphingofungin F的全合成研究
摘要
天然产物鞘氨酸抗菌素(Sphingofungin)类化合物是烟曲酶产生的抗菌代谢物的一种新科,首先在1992年由Merck公司的Van Middlesworth与他的合作者从海洋生物Aspergillus和Paecilomyces中分离得到。这些化合物表达其生物活性有独特的机制,即对丝氨酸十六(烷)酰转移酶(SPT,生物合成鞘酯类的一种很重要的酶)具有很有效的抑制活性。由于其独特的生物活性,有许多化学家对其进行了全和成工作。尽管如此,发展一种更为高效简洁的路线来合成天然产物Sphingofungin类化合物对其研究及应用仍然有很大的化学和生物学意义。
本文就Sphingofungin家族化合物的发现、结构确定及化学合成进行了全面的总结。结合本实验室应用以樟脑为原料合成的三环亚胺内酯在不对称合成α-氨基酸方面的经验,特别是利用Aldol反应合成β-羟基α-氨基酸方面的经验,设计了两条合成路线对天然产物Sphingofungin F经行了全合成的探索并取得了较大的进展。在对天然产物Sphingofungin F的全合成过程中,发展了由内酯一锅法合成末端羟基酮的方法学并应用于全和成工作,有效的提高了全合成的效率。另外,还发展了利用格氏试剂异丙基溴化镁为试剂,以甲醇钠为催化剂一锅法高产率的由内酯合成末端羟基酰胺的方法,为酰胺的合成以及Weinreb酰胺的合成提供了另外一条高效的途径。本文的主要内容有:
1.在实验室对三环亚胺内酯合成路线的基础上进行了条件优化,提高了手性氨基酸辅助基的合成效率,并合成了天然产物中的重要片段甲基化的三环亚胺内酯。
2.发展了由内酯为原料,以甲醇钠为催化剂,一锅法合成末端羟基酮的方法。以不同的内酯与不同的格氏试剂反应,研究了这个反应的适用性,并均得到了很好的结果。在由核糖衍生的内酯的反应中发现了开环又重新关环的反应,探索了其反应机理,以单晶衍射确定了其产物构型,发展了一种合成与文献中构型相反的化合物的新方法。
3.发展了以内酯为原料、以异丙基溴化镁为试剂、甲醇钠为催化剂一锅法合成Weinreb酰胺或其他酰胺的方法学,为末端羟基酰胺的合成提供了一条有效的途经。
4.利用我们发展的一锅法制备内酯的方法合成了天然产物中的一个重要片段砜,并以L-(+)酒石酸为起始原料合成了另外一个重要片段不同保护的烯丙基溴。尝试了偶联反应并均取得了成功。成功将所得的偶联产物转化为全和成中所需要的重要片段醛。
5.研究了醛与甲基化三环亚胺内酯的Aldol反应条件,并将其应用于天然产物的全和成中成功得到了目标产物,将其进一步水解除去手性辅助基并脱掉保护基即可完成对天然产物Sphingofungin F的全和成工作。
Sphingofungins are a new class of antifungal agents isolated from Aspergillus and Paecilomyces and are reported to be potent and specific inhibitors of serine palmitoyl transferase(SPT).These naturally occurring SPT inhibitors also have attractive pharmacological potential since they possess fungicidal and immunosuppressive activity,although the latter activity is apparently not a consequence of inhibition of SPT.The structure elucidation study revealed that sphingofungins are novel polyhydroxy amino acid derivatives bearing a C_(20) straight carbon chain with E-olefin and four contiguous asymmetric centers.
Therefore,numerous methods to synthesize these compounds have been reported. In this thesis,the development for the chemical synthesis of Sphingofungin was reviewed.In our laboratory,we have reported two novel chiral tricyclic iminolactones, prepared from(1R)-(+)-camphor as glycine equivalents,which have been successfully applied to the asymmetric synthesis of or-substitutedα-amino acids andβ-hydroxyα-amino acid.Two synthesis stragies toward Sphingofungin F using Aldol reaction of aldehyde and methyl tricyclic iminolactone were researched in this thesis and one of them was found effectively.
We have developed a convenient one-pot methodology for the synthesis ofω-hydroxyketones from commercially available lactones and Grignard regents in good yields.The one-pot reaction that Grignard regents added to lactones to affordω-hydroxyketones using NaOCH_3 as catalyst is first reported.We found some new cyclic compounds via hydroxyketone.The reaction mechanism was researched and the configuration was charactered by X-ray.
We have developed an efficient,generally high-yields(up to 98%) method to generate amides.The reaction is most easily executed when THF was used as solvent, and isopropyl magnesium bromide as base.NaOCH_3 can promote the reaction rate and yield.The present method constitutes an important modification to the well known Weinreb methodology.This method can be used to synthesize other amides with hydroxyl group in good yield.
The necessary key compound sulfone was synthesized using our strategy of one-pot reaction fromε-Caprolactone.Two deferent protected allylic bromides were obtained from L-(+)-tartaric acid.The coupling reactions were explerored and the desire target compounds was obtained.The key compound adehyde was got by chemical transform the coupling product.The Aldol reaction of aldehyde and the methyl tricyclic iminolactone was detected and the good result was observed.Hydroxylation of the Aodol product could complete the syntheses of the natural product Sphingofungin F.
本文就Sphingofungin家族化合物的发现、结构确定及化学合成进行了全面的总结。结合本实验室应用以樟脑为原料合成的三环亚胺内酯在不对称合成α-氨基酸方面的经验,特别是利用Aldol反应合成β-羟基α-氨基酸方面的经验,设计了两条合成路线对天然产物Sphingofungin F经行了全合成的探索并取得了较大的进展。在对天然产物Sphingofungin F的全合成过程中,发展了由内酯一锅法合成末端羟基酮的方法学并应用于全和成工作,有效的提高了全合成的效率。另外,还发展了利用格氏试剂异丙基溴化镁为试剂,以甲醇钠为催化剂一锅法高产率的由内酯合成末端羟基酰胺的方法,为酰胺的合成以及Weinreb酰胺的合成提供了另外一条高效的途径。本文的主要内容有:
1.在实验室对三环亚胺内酯合成路线的基础上进行了条件优化,提高了手性氨基酸辅助基的合成效率,并合成了天然产物中的重要片段甲基化的三环亚胺内酯。
2.发展了由内酯为原料,以甲醇钠为催化剂,一锅法合成末端羟基酮的方法。以不同的内酯与不同的格氏试剂反应,研究了这个反应的适用性,并均得到了很好的结果。在由核糖衍生的内酯的反应中发现了开环又重新关环的反应,探索了其反应机理,以单晶衍射确定了其产物构型,发展了一种合成与文献中构型相反的化合物的新方法。
3.发展了以内酯为原料、以异丙基溴化镁为试剂、甲醇钠为催化剂一锅法合成Weinreb酰胺或其他酰胺的方法学,为末端羟基酰胺的合成提供了一条有效的途经。
4.利用我们发展的一锅法制备内酯的方法合成了天然产物中的一个重要片段砜,并以L-(+)酒石酸为起始原料合成了另外一个重要片段不同保护的烯丙基溴。尝试了偶联反应并均取得了成功。成功将所得的偶联产物转化为全和成中所需要的重要片段醛。
5.研究了醛与甲基化三环亚胺内酯的Aldol反应条件,并将其应用于天然产物的全和成中成功得到了目标产物,将其进一步水解除去手性辅助基并脱掉保护基即可完成对天然产物Sphingofungin F的全和成工作。
Sphingofungins are a new class of antifungal agents isolated from Aspergillus and Paecilomyces and are reported to be potent and specific inhibitors of serine palmitoyl transferase(SPT).These naturally occurring SPT inhibitors also have attractive pharmacological potential since they possess fungicidal and immunosuppressive activity,although the latter activity is apparently not a consequence of inhibition of SPT.The structure elucidation study revealed that sphingofungins are novel polyhydroxy amino acid derivatives bearing a C_(20) straight carbon chain with E-olefin and four contiguous asymmetric centers.
Therefore,numerous methods to synthesize these compounds have been reported. In this thesis,the development for the chemical synthesis of Sphingofungin was reviewed.In our laboratory,we have reported two novel chiral tricyclic iminolactones, prepared from(1R)-(+)-camphor as glycine equivalents,which have been successfully applied to the asymmetric synthesis of or-substitutedα-amino acids andβ-hydroxyα-amino acid.Two synthesis stragies toward Sphingofungin F using Aldol reaction of aldehyde and methyl tricyclic iminolactone were researched in this thesis and one of them was found effectively.
We have developed a convenient one-pot methodology for the synthesis ofω-hydroxyketones from commercially available lactones and Grignard regents in good yields.The one-pot reaction that Grignard regents added to lactones to affordω-hydroxyketones using NaOCH_3 as catalyst is first reported.We found some new cyclic compounds via hydroxyketone.The reaction mechanism was researched and the configuration was charactered by X-ray.
We have developed an efficient,generally high-yields(up to 98%) method to generate amides.The reaction is most easily executed when THF was used as solvent, and isopropyl magnesium bromide as base.NaOCH_3 can promote the reaction rate and yield.The present method constitutes an important modification to the well known Weinreb methodology.This method can be used to synthesize other amides with hydroxyl group in good yield.
The necessary key compound sulfone was synthesized using our strategy of one-pot reaction fromε-Caprolactone.Two deferent protected allylic bromides were obtained from L-(+)-tartaric acid.The coupling reactions were explerored and the desire target compounds was obtained.The key compound adehyde was got by chemical transform the coupling product.The Aldol reaction of aldehyde and the methyl tricyclic iminolactone was detected and the good result was observed.Hydroxylation of the Aodol product could complete the syntheses of the natural product Sphingofungin F.
引文
1.(a) Barrett, G C (Ed.).Chemistry and Biochemistry of the Amino Acids; Chapman and Hall, London 1985.(b) Jones, J.H.(Sen.Reporter) Amino Acids and Peptides, Specialist Periodical Report; The Royal Society of Chemistry 1992;Volume 23 (Literature published in 1990), and previous volumes.
2.(a) Bell, E.A.The Non-protein Amino Acids of Higher Plants in Endeavour 1980,Vol.4 (New Series), 102-108.(b) Wagner, I.; Musso, H.Angew.Chem.1983, 95,827.New Naturally Occurring Amino Acids; Angew.Chem.; Int.Ed.Engl.1983,22, 816.(c) Hunt, S.in Chemistry and Biochemistry of the Amino Acids; Barrett,G C.(Ed.).Chapman and Hall, London 1985, Chapter 4,55-138.
3.(a) Merrill, A.H., Jr.; Sweeley, C.C.In Biochemistry of Lipids, Lipoproteins and Membranes, Vance, D.E., Vance, J., Eds; Elsevier Science B.V.: Amsterdam,1996, pp 309-339.(b) Characterization of enzymatic synthesis of sphingolipid long-chain bases in Saccharomyces cerevisiae: mutant strains exhibiting long-chain-base auxotrophy are deficient in serine palmitoyltransferase activity;Pinto, W.J., Wells, G.W., Lester, R.L.J.Bacteriol.1992,174, 2575-2581.
4.(a) VanMiddlesworth, F.; Giacobbe, R.A.; Lopez, M.; Garrity, G; Bland, J.A.;Bartizal, K.; Fromfling, R.A.; Polishook, J.; Zweerink, M.; Edison, A.M.;Rozdilsky, W.; Wilson, K.E.; Monaghan, R.L.Sphingofungins A, B, C, and D; a new family of antifungal agents.I.Fermentation, isolation, and biological activity.J.Antibiot.1992, 45, 861-867.(b) Characterization of a novel, potent, and specific inhibitor of serine palmitoyltransferase; Zweerink, M.M.; Edison, A.M.;Well, G.B.; Pinto, W.; Lester, R.L.J.Biol.Chem.1992, 267, 25032-25038.Structure elucidation: (c) Determination of the relative and absolute stereochemistry of sphingofungins A, B, C, and D.VanMiddlesworth, F.; Dufresne, C; Wincott, F.E.; Mosley, R.T.; Wilson, K.E.Tetrahedron Lett.1992,33, 297-300.
5.Payette, D.R.; Just, G.A total synthesis of the enantiomer of anhydromyriocin (anhydrothermozymocidin); Can.J.Chem.1981,59, 269-282.
6.Asymmetric Total Synthesis of ISP-I(Myriocin,Thermozymocidin),a Potent Immunosuppressive Principle in the Isaria sinclairii Metabolite;Sano,S.;Kobayashi,Y.;Kondo,T.;Takebayashi,M.;Maruyama,S.;Fujita,T.;Nagao,Y.Tetrahedron Lett.1995,36,2097-2100.
7.An Efficient and Convenient Approach to the Total Synthesis of Sphingofungin;Liu,Ding-Guo;Wang,Bing;Lin,Guo-Qiang.J.Org.Chem 2000,65,9114-9119.
8.Total Synthesis of(+)-Myriocin and(-)-Sphingofungin E from Aldohexoses Using Overman Rearrangement as the Key Reaction Oishi,T.;Ando,K.;Inomiya,K.;Sato,H.;Iida,M.;Chida,N.Bulletin of the Chemical Society of Japan 2002,75,1927-1947.
9.An enantio- and stereocontrolled synthesis of(-)-mycestericin E via cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction;Iwabuchi,Y.;Furukawa,M.;Esumi,T.;Hatakeyama,S.Chem.Commun.2001,2030.
10.(a) A New Strategy for the Synthesis of Sphingosine Analogs.Sphingofungin F Trost,B.M.;Lee,C-B.J.Am Chem Soc.1998,120,6818-6819.
(b)gem-Diacetates as Carbonyl Surrogates for Asymmetric Synthesis.Total Syntheses of Sphingofungins E and F;Trost,B.M.;Lee,C-B.J.Am.Chem.Soc.2001,123,12191-12201.
(c) Total Synthesis of Myriocin;Lee,K.-Y.;Oh,C.-Y.;Kim,Y.-H.;Joo,J,-E.;Ham,W.-H.Tetrahedron Lett.2002,43,9361-9363.
11.Ester Dienolate[2,3]-Wittig Rearrangement in Natural Product Synthesis:Diastereoselective Total Synthesis of the Triester of Viridiofungin A,A2,and A4;Pollex,A.;Millet,A.;M(u|")ller,J.;Hiersemann,M.;Abraham,L.J.Org.Chem.2005,70,5579-5591.
12.Catalytic Asymmetric Syntheses of Antifungal Sphingofungins and Their Biological Activity as Potent Inhibitors of Serine Palmitoyltransferase(SPT);Kobayashi,S.;Furuta,T.;Hayashi,T.;Nishijima,M.;Hanada,K.J.Am Chem Soc.1998,120,908-919.
13.Use of heterocycles as chiral ligands and auxiliaries in asymmetric syntheses of sphingosine,sphingofungins B and F;Kobayashi,S.;Furuta,T.Tetrahedron 1998,54,10275-10294.
14.Synthesis of sphingosine relatives.Part 21.Synthesis of sphingofungin D and its three diastereomers;Otaka,K.;Mori,K.Eur.J.Org.Chem.1999,1795-1802.
15.Total Synthesis of(+)-Myriocin and(-)-Sphingofungin E from Aldohexoses Using Overman Rearrangement as the Key Reaction;Oishi,T.;Ando,K.;Inomiya,K.;Sato,H.;lida,M.;Chida,N.;Bull.Chem.Soc.Jpn 2002,75,1927-1947.
16.Total synthesis of sphingofungin E from D-glucose derivative;Nakamura,T.;Shiozaki,M.;Tetrahedron.2002.58.8779-8791.
17.Total synthesis of sphingofungin F;Li,M.;Wu,A-M.Synlett,2006,18,2985-2988.
18.The first total synthesis of sphingofungin E and the determination of its stereochemistry;Wang,B.;Yu,X-M;Lin,G-Q;Synlett,2001,904-906
19.Total Synthesis of Sphingofungin F;Lee,K-Y;Oh,C-Y;Ham,W-H.Suwon,S.Korea.Org.Lett.,2002,4,4403-4405.
20.Synthesis of sphingofungin D and its stereoisomer at C-14;Mori,K.;Otaka,K.Tetrahedron Lett.1994,35,9207-10.
21.(a) Total synthesis of(+)-myriocin and(-)-sphingofungin E from aldohexoses using Overman rearrangement as the key reaction.Takeshi,O.;Koji,A.;Kenjin I.;Hideyuki,S.;Masatoshi,I.;Noritaka,C.;Bull.Chem.Soc.Jpn.2002,75,1927-1947.
(b)Total Synthesis of Sphingofungin E from D-Glucose.Takeshi,O.;Koji,A.;Kenjin I.;Hideyuki,S.;Masatoshi,I.;Noritaka,C.;Org.Lett.2002,4,151-154.
22.Asymmetric synthesis of antifungal agents sphingofungins using catalytic asymmetric aldol reactions.Kobayashi,S.;Hayashi,T.;Iwamoto,S.;Furuta,Takayuki;Matsumura,Masae.Synlett.1996,7,672-674.
23.Total synthesis of sphingofungin E.Nakamura,T.;Shiozaki,M.Tetrahedron Lett.2001,42,2701-2704.
1.Burgstahler,A.W.;Weigel,L O.;Sanders M.E.;Shaefer,C.G.;Bell,W.J.Vuturo,S.B.;Synthesis and activity of 29-hydroxy-3,11-dimethyl-2- nonacosa-none,component B of the German cockroach sex pheromone;J.Org.Chem.,1977,42,566-568.
2.Machinaga,N.;Kibayashi C.;Synthesis and Activity of 29-Hydroxy-3,11-dimethyl-2-nonacosanone,Component B of the German Cockroach Sex Pheromone;J.Org.Chem.;1991,56,1386-1393.
3.(a) Dess,D.B.;Martin,J.C.;Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones;J.Org.Soc.,1983,48,4155-4156;
(b) Hu,T.;Schaus,J.V.;Lam,K.;Palfreyman,M.G.;Wuonola,M.;Gustafson,G.;Panek,J.S.Total Synthesis and Preliminary Antibacterial Evaluation of the RNA Polymerase Inhibitors(±)-Myxopyronin A and B;J.Org.Chem.,1998,63,2401-2406.
(c) Smith,A.B.,Ⅲ;Safonov,I.G.Total Synthesis of(+)-Dactylolide;Org.Lett.,2002,4,635-637.
(d) Yadav,J.S.;Reddy,B.V.S.;Basak,A.K.;Narsaiah,A.V.;Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents;Tetrahedron,2004,60,2131-2135.
(e)O'Neil,G.W.;Phillips,A.J.Total Synthesis of(-)-Dictyostatin,J.Am.Chem.Soc.;2006,128,5340-5341.
(f) Ghosh,A.K.;Gong,G.Enantioselective Total Synthesis of Macrolide Antitumor Agent(-)-Lasonolide A;Org.Lett.,2007;9,1437-1440.
4.(a) Kozikowski,A.P.;Lee,J.;A synthetic approach to the cis-fused marine pyranopyrans,(3E)- and(3Z)-dactomelyne.X-ray structure of a rare organomercurial;J.Org.Chem.,1990,55,863-870.
(b) GU,Y-C.;Roughton,A.L.;Seoucy,P.;Goldstein,S.;Eslongchamps P.;Stereocontrolled construction of 1,7-dimethyl A.B.C.[6.6.6]tricycles.Part 11.Transannular Diels-Alder reaction of 14-membered macrocyclescontaining cis-dienophiles;Can.J.Chem.1993,71,1169-1182
5.(a) Dominique, A.; Alexandre, L.F.; Veronique, B.; Christophe, M., Cossy J.; Synthesis of an analog of mycothiazole and total synthesis of pseudotrienic acid B.Pure and Applied Chemistry; 2007, 79, 677-684.(b) Zhang, D-H; Joseph, R.M.; Directed Hydrozirconation of Propargylic Alcohols; J.Am.Chem.Soc.2007,129, 12088-12089.(c) Aarnoud, D.; Jennifer, W.; Kerstin, K.; Wilhelm, B.;Thomas, K..Synthesis of (S)-nonacosan-lO-ol, the major component of tubular plant wax crystals.Eur.J.Org.Chem.2007,21,3508-3511.
6.(a) Whitmore, F.C; Randall, D.I.; Abnormal Grignard reactions.XI.Sterically hindered aliphatic carbonyl compounds.1.Ketones containing the ethyl-tert-butylneopentylcarbinyl group and their bromomagnesium enolates; J.Am.Chem.Soc.1942, 69, 1242-1246.(b) James, C; Kraus, K.W.Ketone synthesis by the Grignard reaction with acid chlorides in presence of ferric chloride.J.Org.Chem.1961,26,1768-1772.(c) Dubois, J.E.; Boussu, M.; Lion, C.Optimal conditions for the synthesis of hindered aliphatic ketones.Catalytic orientation of the condensation of RLi or RMgX-R'COCl by cuprous halides.Tetrahedron Lett.1971, 12, 829-832.(d) Cahiez, G.; Masuda, A.; Bernard, D.;Normant, J.F.Reactivity of organomanganese derivatives.I.Action on acid hlorides.Synthesis of ketones.Tetrahedron Lett.1976, 36, 3155-3156.(e)Fumie, S.; Masaya, I.; Kaoru, O.; Masao, S.; Preparation of ketones by direct reaction of Grignard reagents with acid chlorides in tetrahydrofuran; Tetrahedron Lett.1979, 44, 4303-4306.(g) Zhang, H-H; Zhang, J-W; Guo, Q-Z.Selective coupling reactions of Grignard reagents with acyl halides by copper complexes catalysis - Synthesis of straight chain ketones; Youji Huaxue, 1989,9,73-75.
7.Taillier, C; Bellosta, V.; Meyer, C; Cossy, J.Synthesis of co-Hydroxy Ketones from ω-Benzyloxy Weinreb Amides by Using a Chemoselective Nucleophilic Addition/Birch Reduction Process; Org.Lett.2004,6,2145-2147.
8.Nahm, S.; Weinreb, S.N-methoxy-N-methylamides as effective acylating agents; Tetrahedron Lett.1981,22, 3815-3818.
9.(a) Mentzel, M.; Hoffmann, H.M.R.N-Methoxy N-methyl amides (Weinreb amides) in modern organic synthesis.J.Prakt.Chem.1997, 339, 517-524; (b) Singh,J.;Satyamurthi,N.;Aidhen,I.S.The Growing Synthetic Utility of Weinreb's Amide;J.Prakt.Chem.2000,342,340-347.
10.Williams,J.M.;Jobson,R..B.;Yasuda,N.;Marchesini,G.;Dolling,Ulf-H.;Grabowski,E.J.J.A new general method for preparation of N-methoxy-N-methylamides.Application in direct conversion of an ester to a ketone;Tetrahedron Lett.1995,36,5461-5464.
11.Fujiwara,K.;Amano,A.;Tokiwano T.;Murai,A.;Novel Oxepane Formation by TiCl_4-Catalyzed Nucleophilic Cleavage of 1-Alkoxymethyl-6,8-dioxabicyclo[3.2.1]octanes;Tetrahedron.2000,56,1065-1080.
12.Hanessian,Stephen.;Marcotte,S.;Machaalani,R.;Huang,G-B.;Total Synthesis and Structural Confirmation of Malayamycin A:A Novel Bicyclic C-Nucleoside from Streptomyces malaysiensis;Org.Lett.2004,6,2145-2147.
13.Hisler,K,Tripoli,R.;Murphy,J.A.Reactions of Weinreb amides:formation of aldehydes by Wittig reactions,Tetrahedron Lett.2006,47,6293-6295
14.Conrad.K.;Hsiao.Y.;Miller.R.A practical one-pot process for a-amino aryl ketone synthesis,Tetrahedron Lett.2005,46,8587-8589
15.Bariau,A.;Canet,J-L.;Chalard,P.;Troin,Y.Asymmetric synthesis of 1,3-aminoketals,Tetrahedron:Asymmetry,2005,16,3650-3660
16.Alberola,A.;Ortega,A.G.;Sidaba,M.L.;Safiudo,C.;Versatility of Weinreb amides in the Knorr pyrrole synthesis,Tetrahedron 1999,55,6555-6566
17.Dickson,H,D.;Smith S,C.;Hinkle K.W.A convenient scalable one-pot conversion of esters and Weinreb amides to terminal alkynes;Tetrahedron Lett.2004,45,5597-5599
18.Hirner,S.;Panknin,O.;Edefuhr,M.;Somfai,P.Synthesis of Aryl Glycines by the Arylation of Weinreb Amides;Angew.Chem.Int.Ed.2008,47,1907-1909
19.Mislin,G.L.;Burger,A.;Abdallah,M.A.Synthesis of new thiazole analogues of pyochelin,a siderophore of Pseudomonas aeruginosa and Burkholderia cepacia.A new conversion of thiazolines into thiazoles;Tetrahedron,2004,60,12139-12145
20.(a) Jaipuri,F.A.;Jofre M.F.;Schwarz K.A.;Pohl N.L.Microwave-assisted cleavage of Weinreb amide for carboxylate protection in the synthesis of a (R)-3-hydroxyalkanoic acid,Tetrahedron Lett.2004,45,4149-4152.
(b)Pearson,C.;Rinehart K.L.;Sugano,M.A novel stereoselective route to some uncommon amino acids,Tetrahedron Lett.1999,40,411-414.
(c)Sawamura,M.;Hamashima,H.;Shinoto,H.;Ito,Y.Asymmetric Michael reaction of an a-cyano Weinreb amide catalyzed by a rhodium complex with trans-chelating chiral diphosphine PhTRAP;Tetrahedron Lett.1995,36,6479-6482
21.Aniello F.D.;Mann,A.;Taddei,M.J.J.;1,3-Stereocontrol with Bromoallenes.Synthesis of N-Boc-ADDA,the Unique Amino Acid Present in Several Inhibitors of Scrine/Threonine Phosphatases;J.Org.Chem.1996,61,4870-4871.
22.Shimizu,T.;Osako,K.;Nakata,T.;Efficient method for preparation of N-methoxy-N-methyl amides by reaction of lactones or esters with Me_2A1C1---MeONHMe·HC1,Tetrahedron Lett.1997,38,2685-2688.
23.Williams,J.M.R.;Jobson,B.;Yasuda,N.Marchesini,G.;Dolling,UH.Grabowski-Edward,J.J.;Anthracylmethyl crown ethers as fluorescence sensors of saxitoxin;Tetrahedron Lett.1995,36,5461-5465.
24.(a) Evans,D.A.;Miller,S.J.Ennis,M.D.Asymmetric synthesis of the benzoquinoid ansamycin antitumor antibiotics:total synthesis of(+)-macbecin,J.Org.Chem.1993,58,471-485.
(b) Evans,D.A.;Black,W.C.Total synthesis of(+)-A83543A[(+)-lepicidin A];J.Am.Chem.Soc.1993,115,4497-4513.
(c)Martin,S.F.;Dodge,J.A.;Burgess,Hartmann,L.E.M.;A formal total synthesis of(+)-macbecin I;J.Org.Chem.1992,57,1070-1072.
(d) Pearson,C.Rinehart,K.L.;Sugano,M.Tetrahedron Lett.1999,40,411.
25.Huang,P-Q.;Zheng,X.;Deng,X-M.DIBAL-H-H2NR and DIBAL-H-HNR_1R_2·HC1 complexes for efficient conversion of lactones and esters to amides;Tetrahedron Lett.2001,42,9039-9041.
1.(a) Chiral Tricyclic Iminolactone Derived from(1R)-(+)-Camphor as a Glycine Equivalent for the Asymmetric Synthesis of α -Amino Acids.Xu,Peng-Fei;Chen,Yuan-Shek;Lin,Shu-I.;Lu,Ta-Jung.J.Org.Chem.2002,67,2309-2314
(b)Xu,Peng-Fei;Lu,Ta-Jung.Selective Synthesis of Either Enantiomer of α -Amino Acids by Switching the Regiochemistry of the Tricyclic Iminolactones Prepared from a Single Chiral Source.J.Org.Chem.2003,68,658-661;
(c) Li,Shuo;Hui,Xin-Ping;Yang,Shao-Bo;Jia,Zhong-Jian;Xu,Peng-Fei;Lu,Ta-Jung.A straightforward route to the asymmetric synthesis of 3,4-diepipolyoxamic acid and its isomers.Tetrahedron:Asymmetry,2005,16,1729-1731;
(d) Asymmetric Synthesis of α,α -Disubstituted α -Amino Acids by Diastereoselective Alkylation of Camphor-Based Tricyclic Iminolactone.Xu,Peng-Fei;Li,Shuo;Lu,Ta-Jung;Wu,Chen-Chang;Fan,Botao;Golfis,Georgia.J.Org.Chem 2006,71,4364-4373.
(e) Zhang,Huan-Huan;Hu,Xiu-Qin;Wang,Xiao;Luo,Yong-Chun;Xu,Peng-Fei.A Convenient Route to Enantiopure 3-Aryl-2,3-diaminopropanoic Acids by Diastereoselective Mannich Reaction of Camphor-Based Tricyclic Iminolactone with Imines.J.Org.Chem.2008,73,3634-3637.
2.Peng-Fei Xu,Qiong Li,Shao-Bo Yang,Zhihui Zhang,Lei Li and Xin-Ping Hui;Diastereo- and Enantioselective Synthesis of β-Hydroxy a-Amino Acids:Application to the Formal Synthesis of(+)-Lactacystin.Angew.Chem.Int.Ed.(prepared).
3.(a) Acyclic stereoselection.23.Lactaldehyde enolate equivalents.Heathcock,C.H.;Pirrung,M.C.;Young,S.,D.;Hagen,J.P.;Jarvi,E.T.;Badertscher,U.;Marki,H.P.;Montgomery,S.H.J.Am.Chem.Soc.1984,106,8161-74;
(b)2,2,5-Trimethyl-l,3-dioxolane-4-carboxaldehyde as a chiral synthon:synthesis of the two enantiomers of methyl 2,3,6-trideoxy-L-threo-hex-2-enopyranoside,key intermediate in the synthesis of daunosamine,and of(+)- and(-)-rhodinose.Stefano,S.J.Org.Chem.1985,50,5865-7
(c) Natural polyene-pyrones.Synthesis of(.)-citreoviral.Bowden,M.C.;Patel,P.;Pattenden,G.Tetrahedron Lett.1985,26,4793-6.
4.Stereoconvergent synthesis of C_1-C_17 and C_18-C_25 fragments of bafilomycin A_1;Yadav,J.S.Reddy,K.B.;Sabitha,G.Tetrahedron,2008,64,1971-1982.
5.4-O-Benzyl-2,3-O-isopropylidene-L-thrcose:a useful building block for stereoselective synthesis of monosacchaddes.Mukaiyama,T.;Suzuki,K.;Yamada,T.;Tabnsa,F.Tetrahedron 1990,46,265-276.
6.(a) The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions.Stereochemistry,mechanism,and selected synthetic aspects;Maryanoff,B.E.;Reitz,A.B.Chem.Rev.1989,89,863-927;
(b) Asymmetric Wittig Type Reactions;Rein,T.;Pedersen,T.M.;Synthesis 2002,579-594.
7.An Efficient and Convenient Approach to the Total Synthesis of Sphingofungin;Liu,Ding-Guo;Wang,Bing;Lin,Guo-Qiang.J.Org.Chem.2000,65,9114-9119.
8.(a) Further investigations concerning the existence of complexes of lithium aluminum hydride and aluminum hydride in diethyl ether and in the solid state;Ashby,E.C.,Prasad,H.S.Inorg.Chem.1976,15,993-995.
(b) Stereocontrolled construction of the hexahydrobenzofuran subunit of the avermectins and-the milbemycins:the Aidol strategy.Hirama,M.;Noda,T.;Ito,S.;Kabuto C.J.Org.Chem.1988,53,706-708.
9.(a) Total Synthesis of Ionophore Antibiotic X-14547A.2.Coupling of the Tetrahydropyran and Tetrahydroindan Systems and Construction of the Butadienyl and Ketopyrrole Moieties.Nicolaou,K.C.Claremon,D.A.Papahatjis,D.P.Magolda,R.L.J.Am.Chem Soc.1981,103,6969-6971;
(b) Total Synthesis and Determination of the Absolute Configuration of Coscinosulfate.A New Selective Inhibitor of Cdc25 Protein Phosphatase.Poigny,S.,Nouri,S.,Chiaroni,A.,Guyot,M.,Samadi,M,;J.Org.Chem.2001,66,7263-7269;
(c)Total Synthesis of(-)-Ratjadone.Williams,D.R.,Ihle,D.C.,Plummer,S.V.;Org.Lett.,2001,3,1383-1386.
(d) Enantioselective Synthesis and Structure Revision of Solandelactone E.Davoren,J.E.,Martin,S.F.J.Am.Chem.Soc.2007,129,510-511.
10.Total Synthesis of (+)-Myriocin and (-)-Sphingofungin E from Aldohexoses Using Overman Rearrangement as the Key Reaction; Oishi,T.; Ando, K.;Inomiya,K.; Sato, H.; Iida, M.; Chida, N.; Bull.Chem.Soc.Jpn 2002, 75,1927-1947.
11.(a) Asymmetric synthesis of antifungal agents sphingofungins using catalytic asymmetric aldol reactions.Kobayashi, S.; Hayashi, T.; Iwamoto, S.; Furuta,Takayuki; Matsumura, Masae.Synlett.1996, 7, 672-674.(b) Use of heterocycles as chiral ligands and auxiliaries in asymmetric syntheses of sphingosine, sphingofungins B and F; Kobayashi, S.; Furuta, T.Tetrahedron 1998, 54, 10275-10294.(c) Catalytic Asymmetric Syntheses of Antifungal Sphingofungins and Their Biological Activity as Potent Inhibitors of Serine Palmitoyltransferase (SPT); Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K.J.Am.Chem.Soc.1998,120,908-919.
2.(a) Bell, E.A.The Non-protein Amino Acids of Higher Plants in Endeavour 1980,Vol.4 (New Series), 102-108.(b) Wagner, I.; Musso, H.Angew.Chem.1983, 95,827.New Naturally Occurring Amino Acids; Angew.Chem.; Int.Ed.Engl.1983,22, 816.(c) Hunt, S.in Chemistry and Biochemistry of the Amino Acids; Barrett,G C.(Ed.).Chapman and Hall, London 1985, Chapter 4,55-138.
3.(a) Merrill, A.H., Jr.; Sweeley, C.C.In Biochemistry of Lipids, Lipoproteins and Membranes, Vance, D.E., Vance, J., Eds; Elsevier Science B.V.: Amsterdam,1996, pp 309-339.(b) Characterization of enzymatic synthesis of sphingolipid long-chain bases in Saccharomyces cerevisiae: mutant strains exhibiting long-chain-base auxotrophy are deficient in serine palmitoyltransferase activity;Pinto, W.J., Wells, G.W., Lester, R.L.J.Bacteriol.1992,174, 2575-2581.
4.(a) VanMiddlesworth, F.; Giacobbe, R.A.; Lopez, M.; Garrity, G; Bland, J.A.;Bartizal, K.; Fromfling, R.A.; Polishook, J.; Zweerink, M.; Edison, A.M.;Rozdilsky, W.; Wilson, K.E.; Monaghan, R.L.Sphingofungins A, B, C, and D; a new family of antifungal agents.I.Fermentation, isolation, and biological activity.J.Antibiot.1992, 45, 861-867.(b) Characterization of a novel, potent, and specific inhibitor of serine palmitoyltransferase; Zweerink, M.M.; Edison, A.M.;Well, G.B.; Pinto, W.; Lester, R.L.J.Biol.Chem.1992, 267, 25032-25038.Structure elucidation: (c) Determination of the relative and absolute stereochemistry of sphingofungins A, B, C, and D.VanMiddlesworth, F.; Dufresne, C; Wincott, F.E.; Mosley, R.T.; Wilson, K.E.Tetrahedron Lett.1992,33, 297-300.
5.Payette, D.R.; Just, G.A total synthesis of the enantiomer of anhydromyriocin (anhydrothermozymocidin); Can.J.Chem.1981,59, 269-282.
6.Asymmetric Total Synthesis of ISP-I(Myriocin,Thermozymocidin),a Potent Immunosuppressive Principle in the Isaria sinclairii Metabolite;Sano,S.;Kobayashi,Y.;Kondo,T.;Takebayashi,M.;Maruyama,S.;Fujita,T.;Nagao,Y.Tetrahedron Lett.1995,36,2097-2100.
7.An Efficient and Convenient Approach to the Total Synthesis of Sphingofungin;Liu,Ding-Guo;Wang,Bing;Lin,Guo-Qiang.J.Org.Chem 2000,65,9114-9119.
8.Total Synthesis of(+)-Myriocin and(-)-Sphingofungin E from Aldohexoses Using Overman Rearrangement as the Key Reaction Oishi,T.;Ando,K.;Inomiya,K.;Sato,H.;Iida,M.;Chida,N.Bulletin of the Chemical Society of Japan 2002,75,1927-1947.
9.An enantio- and stereocontrolled synthesis of(-)-mycestericin E via cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction;Iwabuchi,Y.;Furukawa,M.;Esumi,T.;Hatakeyama,S.Chem.Commun.2001,2030.
10.(a) A New Strategy for the Synthesis of Sphingosine Analogs.Sphingofungin F Trost,B.M.;Lee,C-B.J.Am Chem Soc.1998,120,6818-6819.
(b)gem-Diacetates as Carbonyl Surrogates for Asymmetric Synthesis.Total Syntheses of Sphingofungins E and F;Trost,B.M.;Lee,C-B.J.Am.Chem.Soc.2001,123,12191-12201.
(c) Total Synthesis of Myriocin;Lee,K.-Y.;Oh,C.-Y.;Kim,Y.-H.;Joo,J,-E.;Ham,W.-H.Tetrahedron Lett.2002,43,9361-9363.
11.Ester Dienolate[2,3]-Wittig Rearrangement in Natural Product Synthesis:Diastereoselective Total Synthesis of the Triester of Viridiofungin A,A2,and A4;Pollex,A.;Millet,A.;M(u|")ller,J.;Hiersemann,M.;Abraham,L.J.Org.Chem.2005,70,5579-5591.
12.Catalytic Asymmetric Syntheses of Antifungal Sphingofungins and Their Biological Activity as Potent Inhibitors of Serine Palmitoyltransferase(SPT);Kobayashi,S.;Furuta,T.;Hayashi,T.;Nishijima,M.;Hanada,K.J.Am Chem Soc.1998,120,908-919.
13.Use of heterocycles as chiral ligands and auxiliaries in asymmetric syntheses of sphingosine,sphingofungins B and F;Kobayashi,S.;Furuta,T.Tetrahedron 1998,54,10275-10294.
14.Synthesis of sphingosine relatives.Part 21.Synthesis of sphingofungin D and its three diastereomers;Otaka,K.;Mori,K.Eur.J.Org.Chem.1999,1795-1802.
15.Total Synthesis of(+)-Myriocin and(-)-Sphingofungin E from Aldohexoses Using Overman Rearrangement as the Key Reaction;Oishi,T.;Ando,K.;Inomiya,K.;Sato,H.;lida,M.;Chida,N.;Bull.Chem.Soc.Jpn 2002,75,1927-1947.
16.Total synthesis of sphingofungin E from D-glucose derivative;Nakamura,T.;Shiozaki,M.;Tetrahedron.2002.58.8779-8791.
17.Total synthesis of sphingofungin F;Li,M.;Wu,A-M.Synlett,2006,18,2985-2988.
18.The first total synthesis of sphingofungin E and the determination of its stereochemistry;Wang,B.;Yu,X-M;Lin,G-Q;Synlett,2001,904-906
19.Total Synthesis of Sphingofungin F;Lee,K-Y;Oh,C-Y;Ham,W-H.Suwon,S.Korea.Org.Lett.,2002,4,4403-4405.
20.Synthesis of sphingofungin D and its stereoisomer at C-14;Mori,K.;Otaka,K.Tetrahedron Lett.1994,35,9207-10.
21.(a) Total synthesis of(+)-myriocin and(-)-sphingofungin E from aldohexoses using Overman rearrangement as the key reaction.Takeshi,O.;Koji,A.;Kenjin I.;Hideyuki,S.;Masatoshi,I.;Noritaka,C.;Bull.Chem.Soc.Jpn.2002,75,1927-1947.
(b)Total Synthesis of Sphingofungin E from D-Glucose.Takeshi,O.;Koji,A.;Kenjin I.;Hideyuki,S.;Masatoshi,I.;Noritaka,C.;Org.Lett.2002,4,151-154.
22.Asymmetric synthesis of antifungal agents sphingofungins using catalytic asymmetric aldol reactions.Kobayashi,S.;Hayashi,T.;Iwamoto,S.;Furuta,Takayuki;Matsumura,Masae.Synlett.1996,7,672-674.
23.Total synthesis of sphingofungin E.Nakamura,T.;Shiozaki,M.Tetrahedron Lett.2001,42,2701-2704.
1.Burgstahler,A.W.;Weigel,L O.;Sanders M.E.;Shaefer,C.G.;Bell,W.J.Vuturo,S.B.;Synthesis and activity of 29-hydroxy-3,11-dimethyl-2- nonacosa-none,component B of the German cockroach sex pheromone;J.Org.Chem.,1977,42,566-568.
2.Machinaga,N.;Kibayashi C.;Synthesis and Activity of 29-Hydroxy-3,11-dimethyl-2-nonacosanone,Component B of the German Cockroach Sex Pheromone;J.Org.Chem.;1991,56,1386-1393.
3.(a) Dess,D.B.;Martin,J.C.;Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones;J.Org.Soc.,1983,48,4155-4156;
(b) Hu,T.;Schaus,J.V.;Lam,K.;Palfreyman,M.G.;Wuonola,M.;Gustafson,G.;Panek,J.S.Total Synthesis and Preliminary Antibacterial Evaluation of the RNA Polymerase Inhibitors(±)-Myxopyronin A and B;J.Org.Chem.,1998,63,2401-2406.
(c) Smith,A.B.,Ⅲ;Safonov,I.G.Total Synthesis of(+)-Dactylolide;Org.Lett.,2002,4,635-637.
(d) Yadav,J.S.;Reddy,B.V.S.;Basak,A.K.;Narsaiah,A.V.;Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents;Tetrahedron,2004,60,2131-2135.
(e)O'Neil,G.W.;Phillips,A.J.Total Synthesis of(-)-Dictyostatin,J.Am.Chem.Soc.;2006,128,5340-5341.
(f) Ghosh,A.K.;Gong,G.Enantioselective Total Synthesis of Macrolide Antitumor Agent(-)-Lasonolide A;Org.Lett.,2007;9,1437-1440.
4.(a) Kozikowski,A.P.;Lee,J.;A synthetic approach to the cis-fused marine pyranopyrans,(3E)- and(3Z)-dactomelyne.X-ray structure of a rare organomercurial;J.Org.Chem.,1990,55,863-870.
(b) GU,Y-C.;Roughton,A.L.;Seoucy,P.;Goldstein,S.;Eslongchamps P.;Stereocontrolled construction of 1,7-dimethyl A.B.C.[6.6.6]tricycles.Part 11.Transannular Diels-Alder reaction of 14-membered macrocyclescontaining cis-dienophiles;Can.J.Chem.1993,71,1169-1182
5.(a) Dominique, A.; Alexandre, L.F.; Veronique, B.; Christophe, M., Cossy J.; Synthesis of an analog of mycothiazole and total synthesis of pseudotrienic acid B.Pure and Applied Chemistry; 2007, 79, 677-684.(b) Zhang, D-H; Joseph, R.M.; Directed Hydrozirconation of Propargylic Alcohols; J.Am.Chem.Soc.2007,129, 12088-12089.(c) Aarnoud, D.; Jennifer, W.; Kerstin, K.; Wilhelm, B.;Thomas, K..Synthesis of (S)-nonacosan-lO-ol, the major component of tubular plant wax crystals.Eur.J.Org.Chem.2007,21,3508-3511.
6.(a) Whitmore, F.C; Randall, D.I.; Abnormal Grignard reactions.XI.Sterically hindered aliphatic carbonyl compounds.1.Ketones containing the ethyl-tert-butylneopentylcarbinyl group and their bromomagnesium enolates; J.Am.Chem.Soc.1942, 69, 1242-1246.(b) James, C; Kraus, K.W.Ketone synthesis by the Grignard reaction with acid chlorides in presence of ferric chloride.J.Org.Chem.1961,26,1768-1772.(c) Dubois, J.E.; Boussu, M.; Lion, C.Optimal conditions for the synthesis of hindered aliphatic ketones.Catalytic orientation of the condensation of RLi or RMgX-R'COCl by cuprous halides.Tetrahedron Lett.1971, 12, 829-832.(d) Cahiez, G.; Masuda, A.; Bernard, D.;Normant, J.F.Reactivity of organomanganese derivatives.I.Action on acid hlorides.Synthesis of ketones.Tetrahedron Lett.1976, 36, 3155-3156.(e)Fumie, S.; Masaya, I.; Kaoru, O.; Masao, S.; Preparation of ketones by direct reaction of Grignard reagents with acid chlorides in tetrahydrofuran; Tetrahedron Lett.1979, 44, 4303-4306.(g) Zhang, H-H; Zhang, J-W; Guo, Q-Z.Selective coupling reactions of Grignard reagents with acyl halides by copper complexes catalysis - Synthesis of straight chain ketones; Youji Huaxue, 1989,9,73-75.
7.Taillier, C; Bellosta, V.; Meyer, C; Cossy, J.Synthesis of co-Hydroxy Ketones from ω-Benzyloxy Weinreb Amides by Using a Chemoselective Nucleophilic Addition/Birch Reduction Process; Org.Lett.2004,6,2145-2147.
8.Nahm, S.; Weinreb, S.N-methoxy-N-methylamides as effective acylating agents; Tetrahedron Lett.1981,22, 3815-3818.
9.(a) Mentzel, M.; Hoffmann, H.M.R.N-Methoxy N-methyl amides (Weinreb amides) in modern organic synthesis.J.Prakt.Chem.1997, 339, 517-524; (b) Singh,J.;Satyamurthi,N.;Aidhen,I.S.The Growing Synthetic Utility of Weinreb's Amide;J.Prakt.Chem.2000,342,340-347.
10.Williams,J.M.;Jobson,R..B.;Yasuda,N.;Marchesini,G.;Dolling,Ulf-H.;Grabowski,E.J.J.A new general method for preparation of N-methoxy-N-methylamides.Application in direct conversion of an ester to a ketone;Tetrahedron Lett.1995,36,5461-5464.
11.Fujiwara,K.;Amano,A.;Tokiwano T.;Murai,A.;Novel Oxepane Formation by TiCl_4-Catalyzed Nucleophilic Cleavage of 1-Alkoxymethyl-6,8-dioxabicyclo[3.2.1]octanes;Tetrahedron.2000,56,1065-1080.
12.Hanessian,Stephen.;Marcotte,S.;Machaalani,R.;Huang,G-B.;Total Synthesis and Structural Confirmation of Malayamycin A:A Novel Bicyclic C-Nucleoside from Streptomyces malaysiensis;Org.Lett.2004,6,2145-2147.
13.Hisler,K,Tripoli,R.;Murphy,J.A.Reactions of Weinreb amides:formation of aldehydes by Wittig reactions,Tetrahedron Lett.2006,47,6293-6295
14.Conrad.K.;Hsiao.Y.;Miller.R.A practical one-pot process for a-amino aryl ketone synthesis,Tetrahedron Lett.2005,46,8587-8589
15.Bariau,A.;Canet,J-L.;Chalard,P.;Troin,Y.Asymmetric synthesis of 1,3-aminoketals,Tetrahedron:Asymmetry,2005,16,3650-3660
16.Alberola,A.;Ortega,A.G.;Sidaba,M.L.;Safiudo,C.;Versatility of Weinreb amides in the Knorr pyrrole synthesis,Tetrahedron 1999,55,6555-6566
17.Dickson,H,D.;Smith S,C.;Hinkle K.W.A convenient scalable one-pot conversion of esters and Weinreb amides to terminal alkynes;Tetrahedron Lett.2004,45,5597-5599
18.Hirner,S.;Panknin,O.;Edefuhr,M.;Somfai,P.Synthesis of Aryl Glycines by the Arylation of Weinreb Amides;Angew.Chem.Int.Ed.2008,47,1907-1909
19.Mislin,G.L.;Burger,A.;Abdallah,M.A.Synthesis of new thiazole analogues of pyochelin,a siderophore of Pseudomonas aeruginosa and Burkholderia cepacia.A new conversion of thiazolines into thiazoles;Tetrahedron,2004,60,12139-12145
20.(a) Jaipuri,F.A.;Jofre M.F.;Schwarz K.A.;Pohl N.L.Microwave-assisted cleavage of Weinreb amide for carboxylate protection in the synthesis of a (R)-3-hydroxyalkanoic acid,Tetrahedron Lett.2004,45,4149-4152.
(b)Pearson,C.;Rinehart K.L.;Sugano,M.A novel stereoselective route to some uncommon amino acids,Tetrahedron Lett.1999,40,411-414.
(c)Sawamura,M.;Hamashima,H.;Shinoto,H.;Ito,Y.Asymmetric Michael reaction of an a-cyano Weinreb amide catalyzed by a rhodium complex with trans-chelating chiral diphosphine PhTRAP;Tetrahedron Lett.1995,36,6479-6482
21.Aniello F.D.;Mann,A.;Taddei,M.J.J.;1,3-Stereocontrol with Bromoallenes.Synthesis of N-Boc-ADDA,the Unique Amino Acid Present in Several Inhibitors of Scrine/Threonine Phosphatases;J.Org.Chem.1996,61,4870-4871.
22.Shimizu,T.;Osako,K.;Nakata,T.;Efficient method for preparation of N-methoxy-N-methyl amides by reaction of lactones or esters with Me_2A1C1---MeONHMe·HC1,Tetrahedron Lett.1997,38,2685-2688.
23.Williams,J.M.R.;Jobson,B.;Yasuda,N.Marchesini,G.;Dolling,UH.Grabowski-Edward,J.J.;Anthracylmethyl crown ethers as fluorescence sensors of saxitoxin;Tetrahedron Lett.1995,36,5461-5465.
24.(a) Evans,D.A.;Miller,S.J.Ennis,M.D.Asymmetric synthesis of the benzoquinoid ansamycin antitumor antibiotics:total synthesis of(+)-macbecin,J.Org.Chem.1993,58,471-485.
(b) Evans,D.A.;Black,W.C.Total synthesis of(+)-A83543A[(+)-lepicidin A];J.Am.Chem.Soc.1993,115,4497-4513.
(c)Martin,S.F.;Dodge,J.A.;Burgess,Hartmann,L.E.M.;A formal total synthesis of(+)-macbecin I;J.Org.Chem.1992,57,1070-1072.
(d) Pearson,C.Rinehart,K.L.;Sugano,M.Tetrahedron Lett.1999,40,411.
25.Huang,P-Q.;Zheng,X.;Deng,X-M.DIBAL-H-H2NR and DIBAL-H-HNR_1R_2·HC1 complexes for efficient conversion of lactones and esters to amides;Tetrahedron Lett.2001,42,9039-9041.
1.(a) Chiral Tricyclic Iminolactone Derived from(1R)-(+)-Camphor as a Glycine Equivalent for the Asymmetric Synthesis of α -Amino Acids.Xu,Peng-Fei;Chen,Yuan-Shek;Lin,Shu-I.;Lu,Ta-Jung.J.Org.Chem.2002,67,2309-2314
(b)Xu,Peng-Fei;Lu,Ta-Jung.Selective Synthesis of Either Enantiomer of α -Amino Acids by Switching the Regiochemistry of the Tricyclic Iminolactones Prepared from a Single Chiral Source.J.Org.Chem.2003,68,658-661;
(c) Li,Shuo;Hui,Xin-Ping;Yang,Shao-Bo;Jia,Zhong-Jian;Xu,Peng-Fei;Lu,Ta-Jung.A straightforward route to the asymmetric synthesis of 3,4-diepipolyoxamic acid and its isomers.Tetrahedron:Asymmetry,2005,16,1729-1731;
(d) Asymmetric Synthesis of α,α -Disubstituted α -Amino Acids by Diastereoselective Alkylation of Camphor-Based Tricyclic Iminolactone.Xu,Peng-Fei;Li,Shuo;Lu,Ta-Jung;Wu,Chen-Chang;Fan,Botao;Golfis,Georgia.J.Org.Chem 2006,71,4364-4373.
(e) Zhang,Huan-Huan;Hu,Xiu-Qin;Wang,Xiao;Luo,Yong-Chun;Xu,Peng-Fei.A Convenient Route to Enantiopure 3-Aryl-2,3-diaminopropanoic Acids by Diastereoselective Mannich Reaction of Camphor-Based Tricyclic Iminolactone with Imines.J.Org.Chem.2008,73,3634-3637.
2.Peng-Fei Xu,Qiong Li,Shao-Bo Yang,Zhihui Zhang,Lei Li and Xin-Ping Hui;Diastereo- and Enantioselective Synthesis of β-Hydroxy a-Amino Acids:Application to the Formal Synthesis of(+)-Lactacystin.Angew.Chem.Int.Ed.(prepared).
3.(a) Acyclic stereoselection.23.Lactaldehyde enolate equivalents.Heathcock,C.H.;Pirrung,M.C.;Young,S.,D.;Hagen,J.P.;Jarvi,E.T.;Badertscher,U.;Marki,H.P.;Montgomery,S.H.J.Am.Chem.Soc.1984,106,8161-74;
(b)2,2,5-Trimethyl-l,3-dioxolane-4-carboxaldehyde as a chiral synthon:synthesis of the two enantiomers of methyl 2,3,6-trideoxy-L-threo-hex-2-enopyranoside,key intermediate in the synthesis of daunosamine,and of(+)- and(-)-rhodinose.Stefano,S.J.Org.Chem.1985,50,5865-7
(c) Natural polyene-pyrones.Synthesis of(.)-citreoviral.Bowden,M.C.;Patel,P.;Pattenden,G.Tetrahedron Lett.1985,26,4793-6.
4.Stereoconvergent synthesis of C_1-C_17 and C_18-C_25 fragments of bafilomycin A_1;Yadav,J.S.Reddy,K.B.;Sabitha,G.Tetrahedron,2008,64,1971-1982.
5.4-O-Benzyl-2,3-O-isopropylidene-L-thrcose:a useful building block for stereoselective synthesis of monosacchaddes.Mukaiyama,T.;Suzuki,K.;Yamada,T.;Tabnsa,F.Tetrahedron 1990,46,265-276.
6.(a) The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions.Stereochemistry,mechanism,and selected synthetic aspects;Maryanoff,B.E.;Reitz,A.B.Chem.Rev.1989,89,863-927;
(b) Asymmetric Wittig Type Reactions;Rein,T.;Pedersen,T.M.;Synthesis 2002,579-594.
7.An Efficient and Convenient Approach to the Total Synthesis of Sphingofungin;Liu,Ding-Guo;Wang,Bing;Lin,Guo-Qiang.J.Org.Chem.2000,65,9114-9119.
8.(a) Further investigations concerning the existence of complexes of lithium aluminum hydride and aluminum hydride in diethyl ether and in the solid state;Ashby,E.C.,Prasad,H.S.Inorg.Chem.1976,15,993-995.
(b) Stereocontrolled construction of the hexahydrobenzofuran subunit of the avermectins and-the milbemycins:the Aidol strategy.Hirama,M.;Noda,T.;Ito,S.;Kabuto C.J.Org.Chem.1988,53,706-708.
9.(a) Total Synthesis of Ionophore Antibiotic X-14547A.2.Coupling of the Tetrahydropyran and Tetrahydroindan Systems and Construction of the Butadienyl and Ketopyrrole Moieties.Nicolaou,K.C.Claremon,D.A.Papahatjis,D.P.Magolda,R.L.J.Am.Chem Soc.1981,103,6969-6971;
(b) Total Synthesis and Determination of the Absolute Configuration of Coscinosulfate.A New Selective Inhibitor of Cdc25 Protein Phosphatase.Poigny,S.,Nouri,S.,Chiaroni,A.,Guyot,M.,Samadi,M,;J.Org.Chem.2001,66,7263-7269;
(c)Total Synthesis of(-)-Ratjadone.Williams,D.R.,Ihle,D.C.,Plummer,S.V.;Org.Lett.,2001,3,1383-1386.
(d) Enantioselective Synthesis and Structure Revision of Solandelactone E.Davoren,J.E.,Martin,S.F.J.Am.Chem.Soc.2007,129,510-511.
10.Total Synthesis of (+)-Myriocin and (-)-Sphingofungin E from Aldohexoses Using Overman Rearrangement as the Key Reaction; Oishi,T.; Ando, K.;Inomiya,K.; Sato, H.; Iida, M.; Chida, N.; Bull.Chem.Soc.Jpn 2002, 75,1927-1947.
11.(a) Asymmetric synthesis of antifungal agents sphingofungins using catalytic asymmetric aldol reactions.Kobayashi, S.; Hayashi, T.; Iwamoto, S.; Furuta,Takayuki; Matsumura, Masae.Synlett.1996, 7, 672-674.(b) Use of heterocycles as chiral ligands and auxiliaries in asymmetric syntheses of sphingosine, sphingofungins B and F; Kobayashi, S.; Furuta, T.Tetrahedron 1998, 54, 10275-10294.(c) Catalytic Asymmetric Syntheses of Antifungal Sphingofungins and Their Biological Activity as Potent Inhibitors of Serine Palmitoyltransferase (SPT); Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K.J.Am.Chem.Soc.1998,120,908-919.