Synthetic studies on (+)-ophiobolin A: Asymmetric synthesis of the spirocyclic CD-ring moiety

Naoyoshi Noguchi, Masahisa Nakada

    Research output: Contribution to journalArticle

    41 Citations (Scopus)

    Abstract

    Asymmetric synthesis of the spirocyclic CD-ring moiety of (+)-ophiobolin A is described. Fragment A, which was prepared via pig liver esterase (PLE)-mediated kinetic resolution, and fragment B, which was prepared via diastereoselective allylation and subsequent kinetic iodolactonization, were coupled to afford the allylsilane 2, which was successfully cyclized to the desired spirocyclic CD-ring moiety 1a in the presence of a Lewis acid.

    Original languageEnglish
    Pages (from-to)2039-2042
    Number of pages4
    JournalOrganic Letters
    Volume8
    Issue number10
    DOIs
    Publication statusPublished - 2006 May 11

    Fingerprint

    Allylation
    fragments
    Lewis Acids
    Kinetics
    swine
    rings
    kinetics
    Esterases
    synthesis
    liver
    Liver
    Swine
    acids
    ophiobolin A
    allylsilane

    ASJC Scopus subject areas

    • Molecular Medicine

    Cite this

    Synthetic studies on (+)-ophiobolin A : Asymmetric synthesis of the spirocyclic CD-ring moiety. / Noguchi, Naoyoshi; Nakada, Masahisa.

    In: Organic Letters, Vol. 8, No. 10, 11.05.2006, p. 2039-2042.

    Research output: Contribution to journalArticle

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