Biomimetic total synthesis of gracilioethers B and C

Matthew Norris, Michael Perkins, Erik Sorensen

    Research output: Contribution to journalArticle

    15 Citations (Scopus)

    Abstract

    Total syntheses of the marine polyketide metabolites gracilioethers B and C have been realized in 9 steps (40% overall yield) and 10 steps (34% overall yield), respectively. The [2(5H)-furanylidene]ethanoate (furanylidene) motif was constructed in a transacetalization/dehydration cascade of an advanced β-ketoester intermediate, which was designed to mimic a postulated biosynthetic precursor to the natural products. The relative and absolute configurations of gracilioethers B and C are confirmed as (6R,8R) and (6R,8R,11S), respectively.

    Original languageEnglish
    Pages (from-to)668-671
    Number of pages4
    JournalOrganic Letters
    Volume17
    Issue number3
    DOIs
    Publication statusPublished - 2015

    Fingerprint Dive into the research topics of 'Biomimetic total synthesis of gracilioethers B and C'. Together they form a unique fingerprint.

  • Cite this