Enantioselective total synthesis of (+)-ophiobolin A

Kazuhiro Tsuna, Naoyoshi Noguchi, Masahisa Nakada

    Research output: Contribution to journal › Article

    26 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

    Fingerprint

    Cyclization
    Joining
    Substrates
    ophiobolin A
    ophiobolins

    Keywords

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

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Enantioselective total synthesis of (+)-ophiobolin A. / Tsuna, Kazuhiro; Noguchi, Naoyoshi; Nakada, Masahisa.

    In: Chemistry - A European Journal, Vol. 19, No. 17, 22.04.2013, p. 5476-5486.

    Research output: Contribution to journal › Article

    Tsuna, K, Noguchi, N & Nakada, M 2013, 'Enantioselective total synthesis of (+)-ophiobolin A', Chemistry - A European Journal, vol. 19, no. 17, pp. 5476-5486. https://doi.org/10.1002/chem.201204119
    Tsuna K, Noguchi N, Nakada M. Enantioselective total synthesis of (+)-ophiobolin A. Chemistry - A European Journal. 2013 Apr 22;19(17):5476-5486. https://doi.org/10.1002/chem.201204119
    Tsuna, Kazuhiro ; Noguchi, Naoyoshi ; Nakada, Masahisa. / Enantioselective total synthesis of (+)-ophiobolin A. In: Chemistry - A European Journal. 2013 ; Vol. 19, No. 17. pp. 5476-5486.
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