Enantioselective total synthesis of pinnaic acid and halichlorine

Shu Xu, Daisuke Unabara, Daisuke Uemura, Hirokazu Arimoto

    Research output: Contribution to journalArticle

    19 Citations (Scopus)

    Abstract

    The enantioselective total synthesis of the bioactive marine natural products pinnaic acid and halichlorine is reported in detail. Our total synthesis features the construction of the five-membered ring and C9 and C13 stereogenic centers through a palladium-catalyzed trimethylenemethane [3+2] cyclization; the installation of the nitrogen atom through a regioselective Beckmann rearrangement of a poorly reactive ketone; the stereoselective cyclization of the spiro ring through a four-step, one-pot hydrogenation- cyclization; and efficient connection of the sterically hindered lower chain through a reduced-pressure cross olefin metathesis reaction.

    Original languageEnglish
    Pages (from-to)367-375
    Number of pages9
    JournalChemistry - An Asian Journal
    Volume9
    Issue number1
    DOIs
    Publication statusPublished - 2014 Jan 1

    Keywords

    • cyclization
    • metathesis
    • natural products
    • stereoselectivity
    • total synthesis

    ASJC Scopus subject areas

    • Chemistry(all)
    • Biochemistry
    • Organic Chemistry

    Fingerprint Dive into the research topics of 'Enantioselective total synthesis of pinnaic acid and halichlorine'. Together they form a unique fingerprint.

  • Cite this