Synthesis of 3-Hydroxycephems from Penicillin G through Cyclization of Chlorinated 4-(Phenylsulfonylthio)-2-azetidinones Promoted by a BiCl3/Sn or TiCl4/Sn …

…, M Taniguchi, Y Kameyama, M Monnin, S Torii…

Index: Tanaka; Taniguchi; Kameyama; Monnin; Torii; Sasaoka; Shiroi; Nagao; Yamada; Tokumaru Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 5 p. 1385 - 1391

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Citation Number: 11

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 RuCl 3/HIO 4 and HIO 4/CuSO 4 and reductive cyclization of 1-(1-alkoxycarbonyl-3-chloro-2-hydroxy-1-propenyl)-4-(phenylsulfonylthio)-2- azetidinones on treatment with a newly devised BiCl 3/Sn or TiCl 4/Sn bimetal redox ...