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Communication | Regular issue | Vol 16, No. 1, 1981, pp.65-69
Published online, 1st January, 1970
DOI: 10.3987/R-1981-01-0065
Total Synthesis of (±)-Epithienamycins A and B [(±)-Olivanic Acids NM22380 and 22382]

Tetsuji Kametani,* Shyh-Pyng Huang, Takayasu Nagahara, and Masataka Ihara

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


(±)-3R*-(1’S*-Hydroxyethyl)-4R*-(2’,2’-dimethoxyethyl)-2-azetidinone (6), which was obtained from the 4-methoxycarbonyl-isoxazoline (4) as a major product, was converted into (±)-epi-thienamycins A(2) and B(3) [(±)-olivanic acids MM22380 and 22382] via the carbene insertion reaction. This total synthesis confirms the relative stereochemistry of the natural antibiotics.