Synthesis of (±)-Serralongamine A and the Revised Structure of Huperzine N

Gisela V. Saborit, Caroline Bosch, Teodor Parella, Ben Bradshaw, Josep Bonjoch

    Research output: Contribution to journalArticleResearchpeer-review

    8 Citations (Scopus)


    © 2016 American Chemical Society. A revised structure for the Lycopodium alkaloid huperzine N is proposed and confirmed by synthesis. The key synthetic steps involve an epimerization of a cis-5-oxodecahydroquinoline to the corresponding trans isomer and a coupling, followed by a diastereoselective hydrogenation using Wilkinson's catalyst to incorporate the pyridylmethyl moiety. This route allowed the alkaloid serralongamine A to be synthesized for the first time, and two additional steps led to the revised structure of huperzine N, both products bearing an unusual decahydroquinoline stereostructure.
    Original languageEnglish
    Pages (from-to)2629-2634
    JournalJournal of Organic Chemistry
    Issue number6
    Publication statusPublished - 18 Mar 2016


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