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

    Research output: Contribution to journalArticle

    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

    Fingerprint

    Cyclic Ethers
    Polyketides
    metathesis
    Alkenes
    alkenes
    ethers
    rings
    synthesis
    Biological Products
    examination
    Nuclear magnetic resonance
    nuclear magnetic resonance
    products
    configurations
    phomopsin

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

    Cite this

    Synthesis and structural revision of phomopsin B, a novel polyketide carrying a 10-membered cyclic-ether ring. / Izuchi, Yuko; Koshino, Hiroyuki; Hongo, Yayoi; Kanomata, Nobuhiro; Takahashi, Shunya.

    In: Organic Letters, Vol. 13, No. 13, 01.07.2011, p. 3360-3363.

    Research output: Contribution to journalArticle

    Izuchi, Yuko ; Koshino, Hiroyuki ; Hongo, Yayoi ; Kanomata, Nobuhiro ; Takahashi, Shunya. / Synthesis and structural revision of phomopsin B, a novel polyketide carrying a 10-membered cyclic-ether ring. In: Organic Letters. 2011 ; Vol. 13, No. 13. pp. 3360-3363.
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    AU - Takahashi, Shunya

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