Efficient asymmetric synthesis of abeo-abietane-type diterpenoids by using the intramolecular Heck reaction

J Org Chem. 2010 Jan 1;75(1):190-6. doi: 10.1021/jo901972b.

Abstract

The synthesis of the abeo-abietane-type diterpenoids, i.e., (-)-dichroanal B, (-)-dichroanone, and taiwaniaquinone H, was achieved by using the intramolecular asymmetric Heck reaction. Our synthetic routes required fewer steps and gave a much higher overall yield and ee within shorter steps than those for racemic and antipodal forms reported to date (10, 12, and 13 steps with an overall yield of 50%, 40%, and 39%, and 94%, 98%, and 98% ee, respectively).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abietanes / chemical synthesis*
  • Abietanes / chemistry*
  • Catalysis
  • Cyclization
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Ligands
  • Molecular Structure
  • Stereoisomerism

Substances

  • Abietanes
  • Diterpenes
  • Ligands
  • dichroanal B
  • dichroanone
  • taiwaniaquinone H