Selectivity in reduction of natural furanoheliangolides with Stryker's reagent

Org Biomol Chem. 2011 Sep 7;9(17):6148-53. doi: 10.1039/c1ob05734k. Epub 2011 Jul 18.

Abstract

Reduction of the natural sesquiterpene lactones furanoheliangolides with Stryker's reagent is an effective process for producing eremantholides through a biomimetic pathway. Other reduction products are also formed. Oxygenated functions at C-15 of the furanoheliangolide produce an increase in the velocities of the reactions and reduce the chemoselectivity of the reagent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • Biomimetics
  • Bridged-Ring Compounds / chemistry*
  • Furans / chemistry*
  • Lactones / chemistry
  • Oxidation-Reduction
  • Sesquiterpenes / chemistry
  • Sesterterpenes

Substances

  • Bridged-Ring Compounds
  • Furans
  • Lactones
  • Sesquiterpenes
  • Sesterterpenes
  • furanoheliangolide
  • eremantholide
  • 4-Butyrolactone