Stereoselective synthesis of exocyclic alkenes by Cu-catalyzed allylmagnesiation, Pd-catalyzed alkylation, and Ru-catalyzed ring-closing metathesis: Highly stereoselective synthesis of (Z)- and (E)-γ-bisabolenes

Luigi Anastasia, Yves R. Dumond, Ei Ichi Negishi

Research output: Contribution to journalArticlepeer-review

Abstract

Highly efficient stereoselective syntheses of both (Z)- and (E)-γ-bisabolenes (1) were achieved by ring closing metathesis of stereodefined tetrasubstituted alkenes. Both (Z)- and (E)-tetrasubstituted alkene precursors were obtained by Cu-catalyzed stereoselective addition of allylmagnesium bromide to propargyl alcohols, followed by Pd-catalyzed cross coupling of alkylzinc derivatives. This represents the first application of ring-closing metathesis to the stereoselective synthesis of exocyclic alkenes.

Original languageEnglish
Pages (from-to)3039-3043
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number16
Publication statusPublished - 2001

Keywords

  • Alkylation
  • Asymmetric synthesis
  • Bisabolenes
  • Catalysis
  • Cyclization
  • Natural products

ASJC Scopus subject areas

  • Organic Chemistry

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