Divergent synthetic route to new cyclopenta[c]pyran iridoids: syntheses of jatamanin A, F, G and J, gastrolactone and nepetalactone

Org Biomol Chem. 2016 Jan 28;14(4):1244-51. doi: 10.1039/c5ob02147b. Epub 2015 Dec 8.

Abstract

Six natural iridoids including jatamanin A, F, G and J, gastrolactone and nepetalactone have been synthesized via the efficient transformation of a core cyclopenta[c]pyran intermediate. Key features of the syntheses include the stereoselective construction of the core cyclopenta[c]pyran skeleton of the iridoid lactones via a Pd(0)-catalyzed intramolecular allylic alkylation, and the facile transformation of the common intermediate into natural iridoids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclopentane Monoterpenes
  • Cyclopentanes / chemical synthesis
  • Cyclopentanes / chemistry
  • Iridoids / chemical synthesis*
  • Iridoids / chemistry
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Conformation
  • Pyrones / chemical synthesis
  • Pyrones / chemistry
  • Stereoisomerism

Substances

  • Cyclopentane Monoterpenes
  • Cyclopentanes
  • Iridoids
  • Lactones
  • Pyrones
  • nepetalactone