Synthesis of rumphellaone A via epoxy nitrile cyclization

Takafumi Hirokawa, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    12 Citations (Scopus)

    Abstract

    The first enantioselective total synthesis of rumphellaone A, a cytotoxic 4,5-seco-caryophyllane isolated from the gorgonian coral Rumphella antipathies, has been achieved from a known olefinic alcohol by a 16-step sequence involving Stork's epoxy nitrile cyclization as the key step to concomitantly install a cyclobutane ring and three contiguous stereogenic centers contained in the molecule.

    Original languageEnglish
    Pages (from-to)4581-4587
    Number of pages7
    JournalTetrahedron
    Volume68
    Issue number24
    DOIs
    Publication statusPublished - 2012 Jun 17

    Keywords

    • Cyclobutane
    • Cytotoxic
    • Epoxy nitrile
    • Rumphellaone
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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