Paper
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
Published May 1, 1995 · DOI · Hideo Tanaka, M. Taniguchi, Y. Kameyama
Bulletin of the Chemical Society of Japan
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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 1-(1-alkoxycarbonyl-3-chloro-2-hydroxy-1-propenyl)-4-(phenylsulfonylthio)-2-azetidinones on treatment with a newly devised BiCl3/Sn or TiCl4/Sn bimetal redox couple in DMF containing pyridine.
This novel method allows for the synthesis of 3-hydroxycephems from penicillin G by cleaving C=C bonds and reductive cyclization of chlorinated 4-(phenylsulfonylthio)-2-azetidinones in a BiCl3/S
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