First total synthesis of (+)-indicanone

Org Biomol Chem. 2012 Jun 28;10(24):4747-51. doi: 10.1039/c2ob25500f. Epub 2012 May 15.

Abstract

The first total synthesis of the guaiane-type sesquiterpene, (+)-indicanone (1), isolated from the root of Wikstroemia indica, was accomplished based on the rhodium(I)-catalyzed Pauson-Khand-type reaction of the allenyne derivative, which was derived from (+)-limonene. This total synthesis unambiguously confirmed the complete structure of (+)-indicanone involving its absolute stereochemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Molecular Structure
  • Sesquiterpenes / chemical synthesis*
  • Stereoisomerism
  • Wikstroemia / chemistry

Substances

  • Sesquiterpenes
  • indicanone