Total synthesis of plakilactones C, B and des-hydroxyplakilactone B by the oxidative cleavage of gracilioether furanylidenes

Matthew Norris, Michael Perkins

    Research output: Contribution to journalArticle

    7 Citations (Scopus)

    Abstract

    A chemoselective oxidative cleavage of synthetic gracilioether B, 11-epi-gracilioether C benzoate, and des-hydroxygracilioether C with pyridinium chlorochromate, which proceeds with loss of the furanyl acetate, has enabled total synthesis and stereochemical elucidation of the marine sponge metabolites (4R,6R)-plakilactone C, (4R,6R,9R)-plakilactone B, and (4R,6R)-des-hydroxyplakilactone B. des-Hydroxygracilioether C, the putative biosynthetic precursor to hippolachnin A, was also found to undergo a facile ene cyclization on treatment with SnCl4.

    Original languageEnglish
    Pages (from-to)6848-6854
    Number of pages7
    JournalThe Journal of Organic Chemistry
    Volume81
    Issue number15
    DOIs
    Publication statusPublished - 2016

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