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Communication | Regular issue | Vol 45, No. 7, 1997, pp.1257-1261
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7799
Total Syntheses of N-Trifluoroacetyl-L-daunosamine, N-Trifluoroacetyl-L-acosamine, N-Benzoyl-D-acosamine, and N-Benzoyl-D-ristosamine from an Achiral Precursor, Methyl Sorbate

Machiko Ono, Chikako Saotome, and Hiroyuki Akita*

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan

Abstract

A conjugated addition of benzylamine to methyl (4R,5S)-4,5-(isopropylidenedioxy)-(2E)-hexenoate (12) followed by lactonization under acidic condition proceeds formally to the total syntheses of L-daunasamine (1) and L-acosamine (2). On the other hand, direct conjugated addition of benzylamine to methyl (4S,5S)-4,5-epoxy-(2E)-hexenoate (4) and the subsequent intramolecular nucleophilic attack by ester carbonyl group against epoxy ring of the substrates leads to the formal total syntheses of D-acosamine (2) and D-ristosamine (3).