Complete Stereochemical Assignment of Campechic Acids A and B

Ruri Isaka, Linkai Yu, Makoto Sasaki, Yasuhiro Igarashi, Haruhiko Fuwa

    Research output: Contribution to journalArticlepeer-review

    5 Citations (Scopus)

    Abstract

    Campechic acids A and B are anti-invasive polyketide antibiotics isolated from Streptomyces sp. CHI93 strain. Herein we describe stereoselective synthesis of the C-16-C-30 fragment of campechic acids A and B via a biosynthesis-inspired epoxide-opening cascade and its NMR spectroscopic comparison with the authentic degradation product, resulting in configurational assignment of the C-21, C-24, C-25, and C-28 stereogenic centers and reassignment of the C-18 stereogenic center.

    Original languageEnglish
    Pages (from-to)3638-3647
    Number of pages10
    JournalJournal of Organic Chemistry
    Volume81
    Issue number9
    DOIs
    Publication statusPublished - 2016 May 6

    ASJC Scopus subject areas

    • Organic Chemistry

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