Enantioselective synthesis of (-)-paeonilide

Chem Commun (Camb). 2012 Apr 7;48(28):3457-9. doi: 10.1039/c2cc18172j. Epub 2012 Feb 23.

Abstract

The first enantioselective synthesis of (-)-paeonilide is reported. Starting from inexpensive furan-3-carboxylic acid the targeted monoterpene was obtained in 12 steps via an asymmetric cyclopropanation-lactonization cascade and a stereoselective side chain insertion at an acetal-like position.

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Furans / chemistry*
  • Paeonia
  • Plant Roots
  • Stereoisomerism
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry

Substances

  • Biological Products
  • Furans
  • Terpenes
  • paeonilide