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Communication | Special issue | Vol 11, No. 1, 1978, pp.207-212
Published online, 1st January, 1970
DOI: 10.3987/S(N)-1978-01-0207
Total Synthesis of dl-7-Amino-3-deacetoxycephalosporanic Acid (7-ADCA) Involving a Short Step Synthesis of a 4,5-Dihydro-6H-1,3-thizaine

Toshihiko Hashimoto, Taiichiro Watanabe, Yoichi Kawano, Teruo Tanaka, and Tetsuo Miyadera*

*Chemical Research Laboratories and Analytical & Metabolic Research Laboratories, Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan

Abstract

A 1,3-thiazine, tert-butyl 5-hydroxy-5-methyl-4,5-dihydro-6H-1,3-thiazine-4-carboxylate (VIII) was prepared by a two step process starting from glycine tert-butyl ester (V). Interestingly the thiazine formation proceeded stereoselectively to afford almost exclusively the cis isomer (VIIIa). Utilizing the 1,3-thiazine the title compound (XV) was synthesized by the established synthetic method.