Alternative synthetic approach for (+)-phomopsidin via the highly stereoselective TADA reaction

Nobuyuki Hayashi, Takahiro Suzuki, Kenji Usui, Masahisa Nakada

    Research output: Contribution to journalArticle

    15 Citations (Scopus)

    Abstract

    This manuscript describes an alternative synthetic approach for (+)-phomopsidin, which shows strong inhibitory activity against the assembly of microtubule proteins. We observed that the TADA reaction of the macrolactone 5 with the reversed C11 configuration provided the desired cycloadduct 6 in 86% yield with excellent stereoselectivity (dr=16:1). Luche reduction of the ketone derived from the major product of the TADA reaction resulted in a 91% yield with excellent stereoselectivity (dr=21:1), and the major product was successfully converted to the known compound in the previously reported total synthesis of (+)-phomopsidin, thereby accomplishing the formal total synthesis of (+)-phomopsidin.

    Original languageEnglish
    Pages (from-to)888-895
    Number of pages8
    JournalTetrahedron
    Volume65
    Issue number4
    DOIs
    Publication statusPublished - 2009 Jan 24

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    Stereoselectivity
    Microtubule Proteins
    Ketones
    phomopsidin

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Alternative synthetic approach for (+)-phomopsidin via the highly stereoselective TADA reaction. / Hayashi, Nobuyuki; Suzuki, Takahiro; Usui, Kenji; Nakada, Masahisa.

    In: Tetrahedron, Vol. 65, No. 4, 24.01.2009, p. 888-895.

    Research output: Contribution to journalArticle

    Hayashi, Nobuyuki ; Suzuki, Takahiro ; Usui, Kenji ; Nakada, Masahisa. / Alternative synthetic approach for (+)-phomopsidin via the highly stereoselective TADA reaction. In: Tetrahedron. 2009 ; Vol. 65, No. 4. pp. 888-895.
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