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

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

    研究成果: Article

    33 引用 (Scopus)

    抄録

    (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.

    元の言語English
    ページ（範囲）553-556
    ページ数4
    ジャーナルOrganic Letters
    巻6
    発行部数4
    DOI
    出版物ステータスPublished - 2004 2 19

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    Antimitotic Agents
    Cycloaddition Reaction
    Diels-Alder reactions
    Temperature
    synthesis
    phomopsidin

    ASJC Scopus subject areas

    • Molecular Medicine

    これを引用

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

    ：: Organic Letters, 巻 6, 番号 4, 19.02.2004, p. 553-556.

    研究成果: Article

    Suzuki, T, Usui, K, Miyake, Y, Namikoshi, M & Nakada, M 2004, 'First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin', Organic Letters, 巻. 6, 番号 4, pp. 553-556. https://doi.org/10.1021/ol036338q
    Suzuki T, Usui K, Miyake Y, Namikoshi M, Nakada M. First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin. Organic Letters. 2004 2 19;6(4):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. ：: Organic Letters. 2004 ; 巻 6, 番号 4. pp. 553-556.
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    AU - Nakada, Masahisa

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