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Communication | Regular issue | Vol 26, No. 11, 1987, pp.2841-2844
Published online, 1st January, 1970
DOI: 10.3987/R-1987-11-2841
Synthesis of (S)-N-(Benzyloxy)-4-acetoxymethyl-2-azetidinone, Potential Intermediate for Carbapenem Antibiotics, by Chemomicrobiological Approach

Haruo Yamada, Hajime Sugiyama, and Masahiro Kajiwara

*Department of Medicinal Chemistry, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

(R)-Ethyl 4-t-butoxy-3-hydroxybutanoate, which was prepared by baker’s yeast reduction of ethyl 4-t-butoxy-3-oxobutanoate, was converted to (R)-3-hydroxybutyrolactone. After cleavage of the lactone ring with N-benzyloxyamine, β-lactam cyclization of the hydroxamate was carried out by Mitsunobu procedure with complete inversion of configuration at C-3 to give (S)-N-(benzyloxy)-4-acetoxymethyl-2-azetidinone. The corresponding (R)-azetidinone was also synthesized from natural (S)-malic acid via (S)-3-hydroxybutyrolactone.