Stereochemistry of enacyloxins 1. Absolute configuration of the cyclohexane ring part of enacyloxins, a series of antibiotics from Frateuria sp. W-315

Toshitaka Fujimori, Osamu Nakayama, Hiromasa Kiyota, Yu Ichi Kamijima, Toshihiko Watanabe, Takayuki Oritani

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The stereochemical study of the cyclohexane ring part of enacyloxins (ENXs), a series of antibiotics isolated from Frateuria sp. W-315, was examined. The relative configuration was elucidated by the coupling constant values of the 1H NMR spectrum. The absolute structure was determined to be 1S, 3R, 4S, because the CD spectrum of the corresponding 3,4-dibenzoate derivative showed negative chirality. This conclusion was confirmed by the synthesis of the dibenzoate from tri-O-acetyl-D-glucal.

Original languageEnglish
Pages (from-to)327-330
Number of pages4
JournalHeterocyclic Communications
Volume7
Issue number4
DOIs
Publication statusPublished - Jan 1 2001
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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