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

H Emtenäs; G Soto; S J Hultgren; G R Marshall; F Almqvist

doi:10.1021/ol0059899

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

Org Lett. 2000 Jul 13;2(14):2065-7. doi: 10.1021/ol0059899.

Authors

H Emtenäs¹, G Soto, S J Hultgren, G R Marshall, F Almqvist

Affiliation

¹ Organic Chemistry, Umeâ University, S-901 87 Umeâ, Sweden.

PMID: 10891231
DOI: 10.1021/ol0059899

Abstract

[reaction: see text] Optically active beta-lactams 3 are obtained in excellent yields (up to 93%) and with complete stereoselectivity from Meldrum's acid derivatives 1 and Delta(2)-thiazolines 2. A selective reduction to aldehydes 5 (R = Ar or CH(2)Ar) 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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Bacteria / drug effects*
Bacteria / metabolism
Crystallography, X-Ray
Fimbriae, Bacterial / drug effects*
Magnetic Resonance Spectroscopy
Molecular Conformation
Stereoisomerism
beta-Lactams

Substances

Anti-Bacterial Agents
beta-Lactams