Synthetic approach toward antibiotic ezomycins. I. Synthesis of 5-amino-5-deoxyoctofuranose-(1,4) derivatives by henry reaction and their stereochemistry

Osamu Sakanaka, Takashi Ohmori, Shuji Kozaki, Tetsuo Suami, Toshio Ishii, Shigeru Ohba, Yoshihiko Saito

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1753-1759
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume59
Issue number6
DOIs
Publication statusPublished - 1986 Jun

ASJC Scopus subject areas

  • Chemistry(all)

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