MICROBIAL GENERATION OF (2R,3S)-ETHYL AND (2S,3S)-ETHYL 2-BENZAMIDOMETHYL-3-HYDROXYBUTYRATE, A KEY INTERMEDIATE IN THE SYNTHESIS OF (3S,1'R)-3-(1'-HYDROXYETHYL)AZETIDIN-2-ONE

被引:13
作者
FUGANTI, C [1 ]
LANATI, S [1 ]
SERVI, S [1 ]
TAGLIANI, A [1 ]
BEDESCHI, A [1 ]
FRANCESCHI, G [1 ]
机构
[1] FARMITALIA CARLO ERBA SPA,RES & DEV,I-20014 NERVIANO,ITALY
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 19期
关键词
D O I
10.1039/p19930002247
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Microbial reduction of the carbonyl group of the substituted acetoacetate esters 3-6 affords directly, or after Ni-Raney desulfurization, the corresponding enantiomerically pure 3S carbinols of variable diastereoisomeric composition. These compounds are transformed into (3S,1'R)-3-(1'-hydroxyethyl)-azetidin-2-one, a useful intermediate in the synthesis of beta-lactam antibiotics.
引用
收藏
页码:2247 / 2249
页数:3
相关论文
共 19 条
[1]  
AZERAD R, 1992, NATO ADV SCI I C-MAT, V381, P421
[2]   FORMATION OF THE (R)-ENANTIOMERS AND (S)-ENANTIOMERS OF ETHYL 3-HYDROXYBUTANOATE AND OF 1-(1,3-DITHIAN-2-YL)-2-HYDROXYPROPANE BY MICROBIAL REDUCTION [J].
BERNARDI, R ;
CARDILLO, R ;
GHIRINGHELLI, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (07) :460-461
[3]   BIOTRANSFORMATION IN ORGANIC-SYNTHESIS - APPLICATIONS OF YEAST REDUCTION IN THE SYNTHESIS OF 3,5-DIHYDROXY ESTERS OF HIGH OPTICAL PURITY [J].
CHRISTEN, M ;
CROUT, DHG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) :264-266
[4]  
CLAISEN L, 1897, LIEBIGS ANN CHEM, V297, P32
[5]   RECENT DEVELOPMENTS IN THE FIELD OF BETA-LACTAM ANTIBIOTICS [J].
DURCKHEIMER, W ;
BLUMBACH, J ;
LATTRELL, R ;
SCHEUNEMANN, KH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (03) :180-202
[6]  
FRIEDMANN E., 1931, BIO CHEM ZEITSCHR, V243, P125
[7]  
HASHIMA K, 1991, J CHEM SOC CHEM COMM, P609
[8]   PURIFICATION AND PROPERTIES OF ALDEHYDE REDUCTASES FROM YEASTS THAT CONVERT ETHYL 2-ACETAMIDO-3-OXOBUTYRATE TO OPTICALLY-ACTIVE ETHYL 2-ACETAMIDO-3-HYDROXYBUTYRATE [J].
KATO, N ;
FUJIE, M ;
HASEGAWA, M ;
SHIMAO, M ;
KITA, K ;
YANASE, H .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1993, 57 (02) :303-307
[9]   PH3P-(PYS)2-CH3CN AS AN EXCELLENT CONDENSING SYSTEM FOR BETA-LACTAM FORMATION FROM BETA-AMINO ACIDS [J].
KOBAYASHI, S ;
IIMORI, T ;
IZAWA, T ;
OHNO, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2406-2408
[10]  
KURTSMAN ED, Patent No. 488611