Convergent total synthesis of (+)-ophiobolin A

Kazuhiro Tsuna, Naoyoshi Noguchi, Masahisa Nakada

    Research output: Contribution to journalArticle

    25 Citations (Scopus)

    Abstract

    At long last: The enantioselective total synthesis of the title compound, which was isolated in 1958, proceeds by a convergent approach. The assembly of the C,D-ring fragment and the A-ring fragment of the core structure is achieved by employing a Reformatsky-type reaction. The eight-membered carbocyclic B ring is efficiently constructed by a challenging ring-closing metathesis (see scheme).

    Original languageEnglish
    Pages (from-to)9452-9455
    Number of pages4
    JournalAngewandte Chemie - International Edition
    Volume50
    Issue number40
    DOIs
    Publication statusPublished - 2011 Sep 26

    Fingerprint

    urinary gonadotropin fragment
    ophiobolin A

    Keywords

    • cross-coupling
    • natural products
    • ring-closing metathesis
    • sesterterpenes
    • total synthesis

    ASJC Scopus subject areas

    • Chemistry(all)
    • Catalysis

    Cite this

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

    In: Angewandte Chemie - International Edition, Vol. 50, No. 40, 26.09.2011, p. 9452-9455.

    Research output: Contribution to journalArticle

    Tsuna, Kazuhiro ; Noguchi, Naoyoshi ; Nakada, Masahisa. / Convergent total synthesis of (+)-ophiobolin A. In: Angewandte Chemie - International Edition. 2011 ; Vol. 50, No. 40. pp. 9452-9455.
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