Enantioselective total synthesis of (+)-ophiobolin A

Kazuhiro Tsuna, Naoyoshi Noguchi, Masahisa Nakada

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    27 Citations (Scopus)

    Abstract

    The enantioselective total synthesis of (+)-ophiobolin A is described. This total synthesis features the construction of the spiro CD ring of (+)-ophiobolin A through a stereoselective intramolecular Hosomi-Sakurai cyclization reaction, the joining of the A ring to the CD ring by using a reaction reported by Utimoto, and the construction of the ophiobolin eight-membered carbocyclic ring through ring-closing metathesis (RCM), which was performed for the first time in this study. This successful RCM reaction required the use of a substrate that contained either a benzyloxy or a methoxymethoxy group at the C5 position and either an isopropenyl group or its hydroxylated form at the C6 position.

    Original languageEnglish
    Pages (from-to)5476-5486
    Number of pages11
    JournalChemistry - A European Journal
    Volume19
    Issue number17
    DOIs
    Publication statusPublished - 2013 Apr 22

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    Keywords

    • cyclization
    • natural products
    • ophiobolin A
    • spiro compounds
    • total synthesis

    ASJC Scopus subject areas

    • Chemistry(all)

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