Asymmetric synthesis and absolute stereochemistry of a labdane-type diterpenoid isolated from the rhizomes of Isodan yuennanensis

Org Biomol Chem. 2016 Jul 14;14(26):6225-30. doi: 10.1039/c6ob00750c. Epub 2016 Jun 2.

Abstract

The first synthesis of a labdane-type diterpenoid isolated from Isodon yuennanensis was achieved in fourteen steps from commercially available starting material, (+)-sclareolide. The synthesis features the Barton nitrite ester reaction to introduce an oxime at the angular methyl group and the Jones oxidation to construct the lactone segment. By comparison of the optical rotation of our synthetic sample and the natural sample, the absolute stereochemistry of the natural diterpenoid has been determined.

MeSH terms

  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Methacrylates / chemistry*
  • Molecular Conformation
  • Nitrates / chemistry*
  • Rhizome / chemistry*
  • Sodium Fluoride / chemistry*
  • Stereoisomerism

Substances

  • Diterpenes
  • Isodan
  • Methacrylates
  • Nitrates
  • labdane
  • Sodium Fluoride