New strategic intermediate for β-lactam antibiotic synthesis: Allenecarboxylates

Sigero Torii, Hideo Tanaka

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Intra- and inter-molecular Michael addition of allenecarboxylates, derived from penicillins, may offer straightforward synthetic routes to 2-exo-methylenepenams and C(3)-substituted Δ3-cephems. Thus obtained 2-exo-methylenepenams are divergent intermediates for penem and penam families of antibiotics or potent β-lactamase inhibitors. The intermolecular Michael addition of the allenecarboxylates can achieve construction of the cephem framework as well as introduction of various C(3)-substituents, e.g., amino, sulfenyl, chloro, and alkenyl groups. In place of the allenecarboxylates, 3,4-disubstituted 2-[4-(phenylsulfonylthio)-2-oxoazetidin-1-yl]-2-butenoates work as a promising precursor of both the 2-exo-methylenepenams and 3-chloro-Δ3-cephems.

Original languageEnglish
Pages (from-to)941-952
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume54
Issue number11
DOIs
Publication statusPublished - Jan 1 1996

ASJC Scopus subject areas

  • Organic Chemistry

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