Synthesis and structural revision of phomopsin B, a novel polyketide carrying a 10-membered cyclic-ether ring

Yuko Izuchi, Hiroyuki Koshino, Yayoi Hongo, Nobuhiro Kanomata, Shunya Takahashi

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    12 Citations (Scopus)

    Abstract

    Total synthesis of the proposed structure 2 for phomopsin B was achieved by using an intramolecular olefin metathesis as a key step. The spectral data, however, did not match with those of the natural product reported. Re-examination of the reported NMR data led to the structural revision of phomopsin B to known dothiorelone A 18. The R configuration of dothiorelone A was determined by total synthesis through a cross-metathesis with a chiral olefin 19.

    Original languageEnglish
    Pages (from-to)3360-3363
    Number of pages4
    JournalOrganic Letters
    Volume13
    Issue number13
    DOIs
    Publication statusPublished - 2011 Jul 1

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    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

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