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Communication | Regular issue | Vol 43, No. 1, 1996, pp.11-14
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7288
Syntheses of Optically Active, Unusual, and Biologically Important Hydroxy-Amino Acids from D-Glucosamine

Katsuo Shinozaki, Kazuhiro Mizuno, and Yukio Masaki*

*Gifu Pharmaceutical University, 5-6-1 Mitahora-Higashi, Gifu 502, Japan

Abstract

Manipulation of D-glucosamine as a chiral pool including stereoinversion of the C3-hydroxyl group, degradation of the C6-carbon, and/or one carbon homologation at the C1-position realized chiral syntheses of (2S,3S)-dihydroxy-(4S)-amino acid moieties, important structural components of a gastroprotective substance AI-77-B and a group of antitumor substances calyculins.