Prominent Aspects of Electroorganic Synthesis in β‐Lactam Chemistry

Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Norio Saitoh, Takashi Siroi, Junzo Nokami

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The potentiality of electrolysis procedures in the penicillin‐cephalosporin conversion as well as in the direct transform of penicillins into oxazolineazetidinones as an intermediate for the preparation of the sulfur‐free analogues of cephalosporins are discussed. Especially, a chemoselective electrolytic chlorination of methyl group of 3‐methyl‐3‐butenoate moiety of thiazolineazetidinone derived from penicillins, a direct synthesis of 3′‐thiosubstituted cephalosporins from the thiazoline‐azetidinones, an improved synthesis of exomethylenecephams, an efficient route to 3‐chloromethyl‐Δ3‐cephems, electrochemical S‐S bond fission of 4‐(2‐benzothiazolyldithio) azetidinones, a direct transformation of penicillins into oxazoline‐azetidinones by chloride salt‐promoted electrolysis, and a versatile intermediate for new β‐lactam antibiotics are presented.

Original languageEnglish
Pages (from-to)951-965
Number of pages15
JournalBulletin des Sociétés Chimiques Belges
Volume91
Issue number12
DOIs
Publication statusPublished - 1982

ASJC Scopus subject areas

  • Chemistry(all)

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