A convenient synthesis of 2-exo-methylene penam, a potent intermediate for new β-lactam antibiotics synthesis

Hideo Tanaka, Yutaka Kameyama, Atsuko Kosaka, Takahito Yamauchi, Sigeru Torii

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Abstract

A convenient synthesis of 2-exo-methylene penams 1 was performed by transformation of thiazoline-azetidinones, derived from penicillin G, through intramolecular Michael addition. Manipulation of the exo-methylene moiety of 1 opened new entries to 2-oxopenam and 2β-thiomethyl substituted penams, respectively.

Original languageEnglish
Pages (from-to)7445-7448
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number50
DOIs
Publication statusPublished - Dec 9 1991

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Keywords

  • exo-methylene penam
  • intramolecular Michael addition
  • β-lactam antibiotics

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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