21 research outputs found
Expressions 1990
https://openspace.dmacc.edu/expressions/1012/thumbnail.jp
The synthesis of Azadirachtin: a potent insect antifeedant
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[BOND]C14 bond in a stereoselective fashion. The allene which results from this sequence then enables a second critical carbon[BOND]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