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Report | Regular issue | Vol 14, No. 12, 1980, pp.1999-2013
Published online, 1st January, 1970
DOI: 10.3987/R-1980-12-1999
Synthesis of 2-(Phenylthiomethylene)oxapenam Derivatives

Sadao Oida,* Akira Yoshida, and Eiji Ohki

*Exploratory Chemistry Research Laboratories, Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan


Copper-catalysed decomposition of azetidinone diazoketones 3a and 3c, resulted in the formation of 2-(phenylthiomethylene)oxapenams, 7a and 11, respectively. Similarly, decomposition of diazoketone 21b gave a mixture of 19 and 22 whose carboxylation afforded an oxapenam-3-carboxylic acid 23a, a novel clavulanic acid analog.