The synthesis of azadirachtin: a potent insect antifeedant

Chemistry. 2008;14(34):10683-704. doi: 10.1002/chem.200801103.

Abstract

We describe in full the first synthesis of the potent insect antifeedant azadirachtin through a highly convergent approach. An O-alkylation reaction is used to unite decalin ketone and propargylic mesylate fragments, after which a Claisen rearrangement constructs the central C8-C14 bond in a stereoselective fashion. The allene which results from this sequence then enables a second critical carbon-carbon bond forming event whereby the [3.2.1] bicyclic system, present in the natural product, is generated via a 5-exo-radical cyclisation process. Finally, using knowledge gained through our early studies into the reactivity of the natural product, a series of carefully designed steps completes the synthesis of this challenging molecule.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Insecticides / chemical synthesis*
  • Insecticides / chemistry
  • Limonins / chemical synthesis*
  • Limonins / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Insecticides
  • Limonins
  • azadirachtin