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

Hans Emtenäs, Gabe Soto, Scott J. Hultgren, Garland R. Marshall, Fredrik Almqvist

Research output: Contribution to journalArticle

38 Scopus citations

Abstract

matrix presented Optically active β-lactams 3 are obtained in excellent yields (up to 93%) and with complete stereoselectivity from Meldrum's acid derivatives 1 and Δ2-thlazolines 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.

Original languageEnglish
Pages (from-to)2065-2067
Number of pages3
JournalOrganic Letters
Volume2
Issue number14
DOIs
StatePublished - Jul 13 2000

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