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

研究成果: Article査読

24 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1753-1759
ページ数7
ジャーナルBulletin of the Chemical Society of Japan
59
6
DOI
出版ステータスPublished - 1986 6

ASJC Scopus subject areas

  • Chemistry(all)

フィンガープリント 「Synthetic approach toward antibiotic ezomycins. I. Synthesis of 5-amino-5-deoxyoctofuranose-(1,4) derivatives by henry reaction and their stereochemistry」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル