Catalytic enantioselective total syntheses of bakkenolides I, J, and S: Application of a carbene-catalyzed desymmetrization

Eric M. Phillips, John M. Roberts, Karl A. Scheidt

Research output: Contribution to journalArticlepeer-review

69 Scopus citations

Abstract

(Figure presented) A general strategy for the catalytic asymmetric syntheses of the bakkenolides is reported. The key bond-forming step involves an N-heterocyclic carbene catalyzed desymmetrization of a 1,3-diketone to form three new bonds in one step with excellent enantio- and diastereoselectivity. This intramolecular reaction allows direct access to the hydrindane core of the bakkenolide family and enables a facile synthesis of these natural products.

Original languageEnglish (US)
Pages (from-to)2830-2833
Number of pages4
JournalOrganic Letters
Volume12
Issue number12
DOIs
StatePublished - Jun 18 2010

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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