Stereoselective total syntheses of uncommon sesquiterpenoids isolated from Jatropha neopauciflora

Org Lett. 2008 Jun 19;10(12):2385-8. doi: 10.1021/ol800633a. Epub 2008 May 14.

Abstract

The first total syntheses of two tricyclic sesquiterpenes 1 and 2, isolated from Jatropha neopauciflora, were completed from dimethyl D-tartrate in a stereoselective manner. The crucial steps in these syntheses involved not only the Rh(I)-catalyzed Pauson-Khand-type reaction of the allenene derivative leading to the exclusive formation of the bicyclo[4.3.0]nonenone framework possessing an angular methyl group but also a highly stereoselective construction of the isopropylcyclopropane ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Jatropha / chemistry*
  • Molecular Structure
  • Rhodium / chemistry
  • Sesquiterpenes* / chemical synthesis
  • Sesquiterpenes* / chemistry
  • Sesquiterpenes* / isolation & purification

Substances

  • Sesquiterpenes
  • Rhodium