Bulletin of the Chemical Society of Japan

Synthesis of 3-Chloro-. DELTA. 3-cephem-4-carboxylate by Addition/Cyclization of Allenecarboxylate. Copper (II)-Promoted Aerobic Oxidation of Arenesulfinic Acids.

H Tanaka, R Kikuchi, S Torii

Index: Tanaka, Hideo; Kikuchi, Ryo; Torii, Sigeru Bulletin of the Chemical Society of Japan, 1996 , vol. 69, # 5 p. 1391 - 1396

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Citation Number: 8

Abstract

The selective transformation of allenecarboxylate derived from penicillin into 3-chloro-Δ 3- cephem-4-carboxylate was successfully achieved by an addition/cyclization reaction with chloride salts in aerobic media containing a copper (II) catalysts, in which copper (II)- catalyzed aerobic oxidation of in situ generated benzenesulfinate ion into less nucleophilic sulfonate ion prior to the nucleophilic addition of the former ion to the allenecarboxylate ...