Enantioselective total synthesis of pinnaic acid and halichlorine

Shu Xu, Daisuke Unabara, Daisuke Uemura, Hirokazu Arimoto

    Research output: Contribution to journalArticlepeer-review

    25 Citations (Scopus)


    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
    Issue number1
    Publication statusPublished - 2014 Jan


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

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry


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