CHEMOENZYMATIC SYNTHESIS OF THE C-13 SIDE-CHAIN OF TAXOL - OPTICALLY-ACTIVE 3-HYDROXY-4-PHENYL BETA-LACTAM DERIVATIVES

被引：135

作者：

BRIEVA, R ^{[1
]}

CRICH, JZ ^{[1
]}

SIH, CJ ^{[1
]}

机构：

[1] UNIV WISCONSIN, SCH PHARM, MADISON, WI 53706 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 05期

关键词：

D O I：

10.1021/jo00057a018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically-pure 3-hydroxy-4-phenyl beta-lactam derivatives have been successfully prepared via enantioselective hydrolyses and transesterifications of racemic esters and alcohols respectively catalyzed by bacterial lipases. These lipases also catalyzed highly enantioselective cleavage of the beta-lactam ring of (+/-)-10 to yield derivatives of (2R,3S)-phenylisoserine in high enantiomeric excess. The resolved enantiomers are important intermediates in the synthesis of the C-13 side chain of taxol.

引用

页码：1068 / 1075

页数：8

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