SYNTHESIS OF A 4-BETA-CARBOXYETHYL DERIVATIVE OF THIENAMYCIN

被引：8

作者：

BOUTHILLIER, G ^{[1
]}

MASTALERZ, H ^{[1
]}

MENARD, M ^{[1
]}

机构：

[1] BRISTOL MYERS SQUIBB CO,PHARMACEUT RES INST,WALLINGFORD,CT 06492

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(00)76942-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of the 4 beta-carboxyethyl derivative of thienamycin (1) is described. The stereochemistry of the substituent at C-4 of the carbapenem was obtained by equilibration of the ester group in the 1-azabicyclo[4.2.0]octane intermediates, 8 and 9, with base. This favored the 5 alpha-ester (8) which was then transformed into the imide (14). Regioselective opening of the imide with lithium allyloxide gave the azetidinone (15) which was converted into the title compound.

引用

页码：4689 / 4692

页数：4

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