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Report | Regular issue | Vol 20, No. 3, 1983, pp.455-461
Published online, 1st January, 1970
DOI: 10.3987/R-1983-03-0455
Studies on the S1-C2 Bond Cleavage Reaction of Penicillins by Carbene Reaction: Synthesis of Penicillin Derivative

Tetsuji Kametani, Naoaki Kanaya, Tomoko Mochizuki, and Toshio Honda

*Institute of Medicinal Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

Treatment of α-diazomalonate (5) with penicillin derivative (1 - 4) in the presence of a catalytic amount of rhodium acetate brought about the facile S1-C2 bond cleavage reactions in moderate yields. 2-Dicarboxylated penicillin derivative was synthesized by employing the above reaction as a key step.