Total synthesis and structure revision of the marine metabolite palmerolide A

Xin Jiang, Bo Liu, Sylvain Lebreton, Jef K. De Brabander

Research output: Contribution to journalArticle

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Abstract

We describe a highly convergent and flexible synthesis of the novel antarctic marine metabolite palmerolide Aan effort leading to a reformulation of palmerolide A as ent-24, the enantiomer of the C19,C20-bis-epimer of the original proposed structure 1. Our total synthesis features a highly stereoselective vinylogous Mukaiyama aldol reaction to introduce the C19,C20-stereodiad, an efficient Suzuki cross-coupling to install the endocyclic diene unit, and an intramolecular Horner-Wadsworth-Emmons olefination to close the macrocycle. Starting from fragments 2, 3 (ent-3), and 13 (prepared in five to eight steps each, 38-70% overall yield) the synthesis of the proposed structure 1 and the enantiomer of palmerolide A (24) was completed in an additional 14 steps (22 steps longest linear sequence).

Original languageEnglish (US)
Pages (from-to)6386-6387
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number20
DOIs
StatePublished - May 23 2007

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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