New facile enantio- and diastereo-selective syntheses of (-)-triptonide and (-)-triptolide

Org Biomol Chem. 2014 Feb 7;12(5):732-6. doi: 10.1039/c3ob42183j. Epub 2013 Dec 18.

Abstract

A novel formal asymmetric synthesis of (-)-triptonide and (-)-triptolide, featuring a new alternative access to their known key intermediate 4, has been achieved through two synthetic routes in 9 steps with 13.6% total yield and 10 steps with 18.5% overall yield, respectively. This synthesis is scalable and hence has high potential for application to further synthetic elaboration and biologic investigation on such natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry*
  • Epoxy Compounds / chemical synthesis
  • Epoxy Compounds / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Phenanthrenes / chemical synthesis*
  • Phenanthrenes / chemistry*
  • Stereoisomerism
  • Substrate Specificity
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry*

Substances

  • Diterpenes
  • Epoxy Compounds
  • Phenanthrenes
  • Triterpenes
  • triptolide
  • triptonide