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

共 6 条

[1] CHEMISTRY OF PENICILLANIC ACIDS .I. 6,6-DIBROMO- AND 6,6-DI-IODO-DERIVATIVES
CLAYTON, JP
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (16): : 2123 - &
[2] PENEMS, A NEW CLASS OF BETA-LACTAM ANTIBIOTICS - 6-ACYLAMINOPENEM-3-CARBOXYLIC ACIDS
ERNEST, I
GOSTELI, J
GREENGRASS, CW
HOLICK, W
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PFAENDLER, HR
WOODWARD, RB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (26) : 8214 - 8222
[3] GAS CHROMATOGRAPHY OF PENICILLIN + PENICILLANIC ACID ESTERS
EVRARD, E
VANDERHAEGHE, H
CLAESEN, M
[J]. NATURE, 1964, 201 (492) : 1124 - &
[4] KAMIYA T, 1973, TETRAHEDRON LETT, P3001
[5] PENEMS, A NEW CLASS OF BETA-LACTAM ANTIBIOTICS .2. TOTAL SYNTHESIS OF RACEMIC 6-UNSUBSTITUTED REPRESENTATIVES
LANG, M
PRASAD, K
HOLICK, W
GOSTELI, J
ERNEST, I
WOODWARD, RB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (21) : 6296 - 6301
[6] 1973, Patent No. 2230372

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