A stereoselective, Sm(II)-mediated approach to decorated cis-hydrindanes: synthetic studies on faurinone and pleuromutilin

Org Biomol Chem. 2011 Apr 7;9(7):2433-51. doi: 10.1039/c0ob01086c. Epub 2011 Feb 15.

Abstract

The cis-hydrindane motif is found in a number of natural products that display important biological activity. A flexible, stereoselective approach to the framework has been developed that features highly diastereoselective, SmI(2)-mediated cyclisations. The strategy has been exploited in the first synthesis of the proposed structure of faurinone and an approach to the skeleton of the antibacterial natural product, pleuromutilin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemistry
  • Cyclization
  • Diterpenes / chemical synthesis
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Indans / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Oxidation-Reduction
  • Pleuromutilins
  • Polycyclic Compounds
  • Samarium / chemistry*
  • Stereoisomerism

Substances

  • Biological Products
  • Diterpenes
  • Heterocyclic Compounds, 4 or More Rings
  • Indans
  • Polycyclic Compounds
  • faurinone
  • hydrindane
  • Samarium