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 journalArticlepeer-review

    6 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 - 2001

    ASJC Scopus subject areas

    • Organic Chemistry

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