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Communication | Regular issue | Vol 12, No. 10, 1979, pp.1301-1303
Published online, 1st January, 1970
DOI: 10.3987/R-1979-10-1301
■ A Formal Total Synthesis of Thienamycin

Tetsuji Kametani,* Shyh-Pyng Huang, Yukio Suzuki, Shuichi Yokohama, and Masataka Ihara

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Careful hydrolysis of the amino alcohol (3), obtained from trans-4-methoxycarbonyl-3-(2’,2’-dimethoxyethyl)-5-methylisoxazoline (2), followed by treatment with dicyclohexylcarbodiimide gave two trans-azetidinones (4 and its epimer) together with the cis-isomer (5). Reaction of 3 with methylmagnesium iodide yielded the trans-azetidinone (4) along with the cis-one (5). The trans-azetidinone (4) was converted into the alcohol (7) and the thioacetal (8), which had been correlated to thienamycin (1).