Synthesis of 3-hydroxycephems from penicillin G through cyclization of chlorinated 4-(phenylsulfonylthio)-2-azetidinones promoted by a BiCl3/Sn or TiCl4/Sn bimetal redox system

H. Tanaka, M. Taniguchi, Y. Kameyama, M. Monnin, S. Torii, M. Sasaoka, T. Shiroi, S. Nagao, T. Yamada, Y. Tokumaru

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Abstract

A novel access to 3-hydroxycephems was attained from penicillin G via the C=C bond cleavage of 1-(1-alkoxycarbonyl-2-chloromethyl-2-propenyl)-4-(phenylsulfonylthio)- 2-azetidinones by successive treatment with RuCl3/HIO4 and HIO4/CuSO4 and reductive cyclization of I-(I-alkoxycarbonyl-3-chloro-2-hydroxy-1-propenyl)-4-(phenylsulfonylth io)-2-azetidinones on treatment with a newly devised BiCl3/Sn or TiCl4/Sn bimetal redox couple in DMF containing pyridine.

Original languageEnglish
Pages (from-to)1385-1391
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume68
Issue number5
DOIs
Publication statusPublished - May 1 1995

ASJC Scopus subject areas

  • Chemistry(all)

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