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

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

    Research output: Contribution to journalArticle

    33 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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    Antimitotic Agents
    Cycloaddition Reaction
    Diels-Alder reactions
    Temperature
    synthesis
    phomopsidin

    ASJC Scopus subject areas

    • Molecular Medicine

    Cite this

    First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin. / Suzuki, Takahiro; Usui, Kenji; Miyake, Yoshiharu; Namikoshi, Michio; Nakada, Masahisa.

    In: Organic Letters, Vol. 6, No. 4, 19.02.2004, p. 553-556.

    Research output: Contribution to journalArticle

    Suzuki, T, Usui, K, Miyake, Y, Namikoshi, M & Nakada, M 2004, 'First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin', Organic Letters, vol. 6, no. 4, pp. 553-556. https://doi.org/10.1021/ol036338q
    Suzuki, Takahiro ; Usui, Kenji ; Miyake, Yoshiharu ; Namikoshi, Michio ; Nakada, Masahisa. / First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin. In: Organic Letters. 2004 ; Vol. 6, No. 4. pp. 553-556.
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