Postulated biogenesis of WS9885B and progress toward an enantioselective synthesis

Christopher D. Vanderwal, David A. Vosburg, Sven Weiler, Erik J. Sorensen

Research output: Contribution to journalArticle

42 Scopus citations

Abstract

(Matrix presented) WS9885B promotes the assembly of microtubules in vitro and displays cytotoxicity as potent as paclitaxel against several cancer cell lines. In this Letter, we propose a biogenesis for this architecturally complex bacterial metabolite from a much simpler, polyunsaturated precursor. We also present significant progress toward a convergent, enantioselective synthesis of WS9885B. Our work features a chemoselective palladium-catalyzed cross-coupling of two advanced building blocks and an uncommon Claisen-like cyclization.

Original languageEnglish (US)
Pages (from-to)645-648
Number of pages4
JournalOrganic Letters
Volume1
Issue number4
DOIs
StatePublished - Aug 26 1999
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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