Total syntheses of angelicoin A, hericenone J, and hericenol A via migratory prenyl- and geranylation-aromatization sequences

J Org Chem. 2012 Jan 6;77(1):652-7. doi: 10.1021/jo202354j. Epub 2011 Dec 7.

Abstract

A five-step synthesis of the natural product angelicoin A using a late stage highly regioselective palladium(0)-catalyzed decarboxylative prenyl migration and aromatization sequence as the key step is reported. The method was extended with geranyl migration in eight-step total syntheses of hericenone J and hericenol A from geraniol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acyclic Monoterpenes
  • Catalysis
  • Molecular Structure
  • Neoprene / chemistry*
  • Palladium / chemistry
  • Phenols / chemical synthesis*
  • Phenols / chemistry*
  • Stereoisomerism
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry*

Substances

  • Acyclic Monoterpenes
  • Phenols
  • Terpenes
  • hericenol A
  • hericenone J
  • prenyl
  • Palladium
  • Neoprene
  • geraniol