Total synthesis of jiadifenolide

Angew Chem Int Ed Engl. 2014 Jul 7;53(28):7286-9. doi: 10.1002/anie.201404224. Epub 2014 May 23.

Abstract

As a potent neurotrophic agent, the sesquiterpenoid jiadifenolide represents a valuable small-molecule lead for the potential therapeutic treatment of neurodegenerative diseases. A stereocontrolled total synthesis of this densely functionalized natural product is reported, central to which is an adventurous samarium-mediated cyclization reaction to establish the tricyclic core and the adjacent C5 and C6 quaternary stereocenters.

Keywords: cyclization; neurological agents; samarium; terpenoids; total synthesis.

MeSH terms

  • Crystallography, X-Ray
  • Cyclization
  • Molecular Structure
  • Oxidation-Reduction
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Stereoisomerism
  • Vinyl Compounds / chemistry

Substances

  • Sesquiterpenes
  • Vinyl Compounds
  • jiadifenolide