The synthesis of Azadirachtin: a potent insect antifeedant
- S.V. Ley
- A. Abad-Somovilla
- J.C. Anderson
- C. Ayats
- R. Banteli
- E. Beckmann
- A. Boyer
- M.G. Brasca
- A. Brice
- H.B. Broughton
- B.J. Burke
- E. Cleator
- D. Craig
- A.A. Denholm
- R.M. Denton
- T. Durand-Reville
- L.B. Gobbi
- M. Gobel
- B.L. Gray
- R.B. Grossmann
- C.E. Gutteridge
- N. Hahn
- S.L. Harding
- D.C. Jennens
- L. Jennens
- P.J. Lovell
- H.J. Lovell
- M.L. de la Puente
- H.C. Kolb
- W. Koot
- S.L. Maslen
- C.F. McCusker
- A. Mattes
- A.R. Pape
- A. Pinto
- D. Santafianos
- J.S. Scott
- S.C. Smith
- A.Q. Somers
- C.D. Spilling
- F. Stelzer
- P.L. Toogood
- R.M. Turner
- G.E. Veitch
- A. Wood
- C. Zumbrunn
DOIAbstract
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 carboncarbon 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
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