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Paper | Regular issue | Vol 43, No. 3, 1996, pp.555-565
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7292
A Convenient Synthesis of the Five-membered Lactams from D-Arabinose

Yaeko Konda,* Tomomi Machida, Michiko Akaiwa, Kazuyoshi Takeda, and Yoshihiro Harigaya

*School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo 108, Japan

Abstract

Synthesis of the five-membered lactams, (3S,4R,5S)-1-benzoyl- and (3S,4R,5S)-1-benzyloxycarbonyl-5-benzyloxymethyl-3,4-dibenzyloxypyrrolidin-2-ones (3a and 3b) which are the important intermediates for the unsaturated five membered amino acid moiety (2) in carzinophilin (1) was described. Lactams (3a and 3b) were synthesized from 2,3,5-tri-O-benzyl-D-arabinitol (6) by a convenient method in seven steps.