PENEMS, A NEW CLASS OF BETA-LACTAM ANTIBIOTICS .3. SYNTHESIS OF OPTICALLY-ACTIVE 2-METHYL-(5R)-PENEM-3-CARBOXYLIC ACID

被引：74

作者：

ERNEST, I

GOSTELI, J

WOODWARD, RB

机构：

[1] Woodward Research Institute

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1979年 / 101卷 / 21期

关键词：

D O I：

10.1021/ja00515a025

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-Methyl-(5R)-penem-3-carboxylic acid (3) has been synthesized from the natural 6(R)-amino-(5R)-penicillanic acid as an optically active representative of the novel group of 6-unsubstituted penems. It proved to be the biologically active component of the previously reported, racemic, 2-methylpenem-3-carboxylic acid. The general necessity of a 5R(6R) configuration for the biological activity of bicyclic β-lactam antibiotics is briefly discussed. © 1979, American Chemical Society. All rights reserved.

引用

页码：6301 / 6305

页数：5

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[1] PENEMS, A NEW CLASS OF BETA-LACTAM ANTIBIOTICS - 6-ACYLAMINOPENEM-3-CARBOXYLIC ACIDS
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[7] SYNTHESIS OF OPTICALLY-ACTIVE (5R)-2-PENEM-3-CARBOXYLATES FROM PENICILLANIC ACID-DERIVATIVES - NEW POTENT ANTI-BACTERIAL AGENTS
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[9] PENEMS, A NEW CLASS OF BETA-LACTAM ANTIBIOTICS .2. TOTAL SYNTHESIS OF RACEMIC 6-UNSUBSTITUTED REPRESENTATIVES
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