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 journalArticle

29 Citations (Scopus)

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

Fingerprint

metathesis
alkylation
Alkylation
Alkenes
closing
alkenes
rings
synthesis
cross coupling
Bromides
bromides
alcohols
Derivatives

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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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.",
keywords = "Alkylation, Asymmetric synthesis, Bisabolenes, Catalysis, Cyclization, Natural products",
author = "Luigi Anastasia and Dumond, {Yves R.} and Negishi, {Ei Ichi}",
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journal = "Annalen der Pharmacie",
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T1 - Stereoselective synthesis of exocyclic alkenes by Cu-catalyzed allylmagnesiation, Pd-catalyzed alkylation, and Ru-catalyzed ring-closing metathesis

T2 - Highly stereoselective synthesis of (Z)- and (E)-γ-bisabolenes

AU - Anastasia, Luigi

AU - Dumond, Yves R.

AU - Negishi, Ei Ichi

PY - 2001

Y1 - 2001

N2 - 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.

AB - 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.

KW - Alkylation

KW - Asymmetric synthesis

KW - Bisabolenes

KW - Catalysis

KW - Cyclization

KW - Natural products

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