Enantioselective preparation of asymmetrically protected 2-propanoyl-1,3-propanediol derivatives: toward the total synthesis of Kazusamycin A

被引:6
作者
Arai, N
Chikaraishi, N
Ikawa, M
Omura, S
Kuwajima, I
机构
[1] Kitasato Univ, Kitasato Inst Life Sci, Kanagawa 2288555, Japan
[2] Japan Sci & Technol Agcy, CREST, Creat & Funct New Mol & Mol Assemblies, Kanagawa 2288555, Japan
[3] Kitasato Univ, Fac Sci, Dept Chem, Kanagawa 2288555, Japan
关键词
D O I
10.1016/j.tetasy.2004.01.007
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The preparation of enantiomerically pure 2-propanoyl-1,3-propanediol derivatives, key intermediates in our studies on total synthesis of the potent antitumor compound Kazusamycin A are described. After various enzymatic protocols for desymmetrization of the prochiral diol were studied, it was found that these compounds could be prepared in 97-98% ee by means of an enzymatic kinetic resolution. (C) 2004 Published by Elsevier Ltd.
引用
收藏
页码:733 / 741
页数:9
相关论文
共 24 条
[1]   1-Ethoxyvinyl 2-furoate, an efficient acyl donor for the lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted propane-1,3-diols and meso-1,2-diols [J].
Akai, S ;
Naka, T ;
Fujita, T ;
Takebe, Y ;
Kita, Y .
CHEMICAL COMMUNICATIONS, 2000, (16) :1461-1462
[2]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[3]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[4]   Synthesis and lipase-catalyzed asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal acetals [J].
Egri, G ;
Fogassy, E ;
Novak, L ;
Poppe, L .
TETRAHEDRON-ASYMMETRY, 1997, 8 (04) :547-557
[5]   Asymmetric construction of benzylic quaternary carbons by lipase-mediated enantioselective transesterification of prochiral alpha,alpha-disubstituted 1,3-propanediols [J].
Fadel, A ;
Arzel, P .
TETRAHEDRON-ASYMMETRY, 1997, 8 (02) :283-291
[6]   A user-friendly entry to 2-iodoxybenzoic acid (IBX) [J].
Frigerio, M ;
Santagostino, M ;
Sputore, S .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4537-4538
[7]   ENANTIOSELECTIVE TRANSESTERIFICATION OF 2-METHYL-1,3-PROPANEDIOL DERIVATIVES CATALYZED BY PSEUDOMONAS-FLUORESCENS LIPASE IN AN ORGANIC-SOLVENT [J].
GRISENTI, P ;
FERRABOSCHI, P ;
MANZOCCHI, A ;
SANTANIELLO, E .
TETRAHEDRON, 1992, 48 (18) :3827-3834
[8]   AN IMPROVED PROCEDURE FOR THE PREPARATION OF THE DESS-MARTIN PERIODINANE [J].
IRELAND, RE ;
LIU, LB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2899-2899
[9]   STRUCTURAL STUDY OF A NEW ANTITUMOR ANTIBIOTIC, KAZUSAMYCIN [J].
KOMIYAMA, K ;
OKADA, K ;
OKA, H ;
TOMISAKA, S ;
MIYANO, T ;
FUNAYAMA, S ;
UMEZAWA, I .
JOURNAL OF ANTIBIOTICS, 1985, 38 (02) :220-223
[10]   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 [J].
Lundhaug, K ;
Overbeeke, PLA ;
Jongejan, JA ;
Anthonsen, T .
TETRAHEDRON-ASYMMETRY, 1998, 9 (16) :2851-2856