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Communication | Regular issue | Vol 20, No. 6, 1983, pp.1001-1004
Published online, 1st January, 1970
DOI: 10.3987/R-1983-06-1001
Studies Related to β-Lactam Antibiotics. Part 8. A Facile Acid-catalyzed Ring Transformation of 1-Dethia-1-oxa-5-epiisoanhydropenicillins into Oxazolinones

Magoichi Sako, Kazuki Akira, Kosaku Hirota, and Yoshifumi Maki

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

1-Dethia-1-oxa-5-epiisoanhydropenicillin (2) undergoes with ease an acid-catalyzed ring transformation by virtue of the participation of an acylamino side chain to give oxazolinone derivative (4), as a mixture of geometrical isomers, under mild conditions in an excellent yield.