The synthesis of Azadirachtin: a potent insect antifeedant

Ley, S.V. et al. (2008) The synthesis of Azadirachtin: a potent insect antifeedant. Chemistry: A European Journal, 14(34), pp. 10683-10704. (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[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.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Boyer, Dr Alistair
• Authors: Ley, S.V., Abad-Somovilla, A., Anderson, J.C., Ayats, C., Bänteli, R., Beckmann, E., Boyer, A., Brasca, M.G., Brice, A., Broughton, H.B., Burke, B.J., Cleator, E., Craig, D., Denholm, A.A., Denton, R.M., Durand-Reville, T., Gobbi, L.B., Göbel, M., Gray, B.L., Grossmann, R.B., Gutteridge, C.E., Hahn, N., Harding, S.L., Jennens, D.C., Jennens, L., Lovell, P.J., Lovell, H.J., de la Puente, M.L., Kolb, H.C., Koot, W.-J., Maslen, S.L., McCusker, C.F., Mattes, A., Pape, A.R., Pinto, A., Santafianos, D., Scott, J.S., Smith, S.C., Somers, A.Q., Spilling, C.D., Stelzer, F., Toogood, P.L., Turner, R.M., Veitch, G.E., Wood, A., and Zumbrunn, C.
• Subjects: Q Science > QD Chemistry
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Chemistry: A European Journal
• Journal Abbr.: Chem. Eur J.
• ISSN: 0947-6539
• ISSN (Online): 1521-3765
• Published Online: 26 September 2008