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Communication | Special issue | Vol 25, No. 1, 1987, pp.123-128
Published online, 1st January, 1970
DOI: 10.3987/S-1987-01-0123
Efficient Synthesis of a New Penem Antibiotic, Sodium (5R,6S)-2-(2-Fluoroethylthio)-6-[(1R)-1-hydroxyethyl]penem-3-carboxylate

Isao Kawamoto, Rokuro Endo, Kosato Suzuki, and Tadashi Hata

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

Abstract

Two useful routes to sodium (5R,6S)-2-(2-fluoroethylthio)- 6-[(1R)-1-hydroxyethyl]penem-3-carboxylate (1) via trithio-carbonate (3) are reported. An intramolecular Wittig reaction of 6 and an oxalimide cyclization of 9 with phosphite are employed as key steps.