First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin

Takahiro Suzuki, Kenji Usui, Yoshiharu Miyake, Michio Namikoshi, Masahisa Nakada

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    34 Citations (Scopus)

    Abstract

    (Equation presented) The first total synthesis of (+)-phomopsidin has been achieved via a diastereoselective transannular Diels-Alder (TADA) reaction. Key steps in the synthesis include diastereoselective ynone reduction with (-)-α-pinene and 9-BBN, macrocyclization by E-selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction, as well as carbometalation under Wipf's conditions, followed by HWE reaction at low temperature to selectively construct the (E)-1-methylpropenyl and (1E,2E)-4-carboxy-1,3-butadienyl substituents.

    Original languageEnglish
    Pages (from-to)553-556
    Number of pages4
    JournalOrganic Letters
    Volume6
    Issue number4
    DOIs
    Publication statusPublished - 2004 Feb 19

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    ASJC Scopus subject areas

    • Molecular Medicine

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