SYNTHETIC APPROACH TOWARD ANTIBIOTIC EZOMYCINS .1. SYNTHESIS OF 5-AMINO-5-DEOXYOCTOFURANOSE-(1,4) DERIVATIVES BY HENRY REACTION AND THEIR STEREOCHEMISTRY

Ezomycins were discovered in a fermentation beer of Streptomyces species as antibiotics, which consisted of aminoocturonic acid, aminoglucuronic acid and base. As a part of a total synthesis of ezomycins, the title compounds have been synthesized. A KF-catalyzed Henry reaction between a nitropentose and a glyceraldehyde derivative gave a nitro alcohols mixture. Hydrogenation of the intact mixture, followed by 7V-acetylation afforded three diastereomers. The absolute configurations of the newly-introduced chiral centers were established by chemical methods and a X-ray crystal structure analysis. © 1986 The Chemical Society of Japan.