Total synthesis of gibbilimbols A-D

J Org Chem. 2002 Apr 5;67(7):2263-5. doi: 10.1021/jo0162991.

Abstract

Gibbilimbols A-D (1-4) were synthesized in 32-49% yield over four steps from commercially available starting materials. A copper-catalyzed coupling of 4-methoxyphenylmagnesium bromide with various unsaturated alkyl bromides was the key step in assembling the (long-chain alkyl)phenol skeleton.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Chemistry, Organic / methods
  • Copper / chemistry
  • Gas Chromatography-Mass Spectrometry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Piperaceae / chemistry*
  • Plants, Medicinal / chemistry*

Substances

  • Phenols
  • gibbilimbol A
  • gibbilimbol B
  • gibbilimbol C
  • gibbilimbol D
  • Copper