Stereoselective synthesis of optically active β-lactams, potential inhibitors of pilus assembly in pathogenic bacteria

被引：35

作者：

Emtenäs, H

Soto, G

Hultgren, SJ

Marshall, GR

Almqvist, F ^{[1
]}

机构：

[1] Umea Univ, S-90187 Umea, Sweden

[2] Washington Univ, Dept Mol Microbiol, St Louis, MO 63130 USA

[3] Washington Univ, Ctr Mol Design, Dept Mol Biol & Pharmacol, St Louis, MO 63130 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 14期

关键词：

D O I：

10.1021/ol0059899

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS Optically active beta-lactams 3 are obtained in excellent yields (up to 93%) and with complete stereoselectivity from Meidrum's acid derivatives 1 and Delta(2)-thiazolines 2, A selective reduction to aldehydes 5 (R = Ar or CH2Ar) was then accomplished by using DIBAL-H, This rigid framework, with stereochemistry different than that of penicillin, is designed to be a suitable scaffold for the development of compounds inhibiting pilus formation in uropathogenic Escherichia coli.

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页码：2065 / 2067

页数：3

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