Electrooxidative desulfurization/chlorination. A facile synthesis of 4-chloro-2-azetidinones, a potent intermediate for carbapenems

Manabu Kuroboshi, Masayoshi Miyada, Syoichi Tateyama, Hideo Tanaka

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

(3S,4R)-3-(1'(R)-tert-Butyldimethylsilyloxyethyl)-4-chloro-2-azetidinone (2), a potent intermediate for the synthesis of carbapenem antibiotics, was synthesized by thermal ring opening/acylation of (3S,5R,6S)-6-(1'(R)-tert-butyldimethylsilyloxyethyl)penicillanate S-oxide (8) leading to 4-acylthio-2-azetidinone derivative 9 and subsequent removal of the N-substituent followed by electrooxidative desulfurization/chlorination of the C(4)-acylthio moiety.

Original languageEnglish
Pages (from-to)1471-1484
Number of pages14
JournalHeterocycles
Volume76
Issue number2
DOIs
Publication statusPublished - Nov 1 2008

Keywords

  • 4-Chloro-2-azetidinone
  • Carbapenem
  • Electrooxidative Chlorination
  • Electrooxidative Desulfurization/Chlorination
  • Rring Opening

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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