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)

    Abstract

    © 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
    Volume81
    Issue number6
    DOIs
    Publication statusPublished - 18 Mar 2016

    Fingerprint Dive into the research topics of 'Synthesis of (±)-Serralongamine A and the Revised Structure of Huperzine N'. Together they form a unique fingerprint.

    Cite this