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  • Title: The synthesis of azadirachtin: a potent insect antifeedant.
    Author: Ley SV, Abad-Somovilla A, Anderson JC, Ayats C, Bänteli R, Beckmann E, Boyer A, Brasca MG, Brice A, Broughton HB, Burke BJ, Cleator E, Craig D, Denholm AA, Denton RM, Durand-Reville T, Gobbi LB, Göbel M, Gray BL, Grossmann RB, Gutteridge CE, Hahn N, Harding SL, Jennens DC, Jennens L, Lovell PJ, Lovell HJ, de la Puente ML, Kolb HC, Koot WJ, Maslen SL, McCusker CF, Mattes A, Pape AR, Pinto A, Santafianos D, Scott JS, Smith SC, Somers AQ, Spilling CD, Stelzer F, Toogood PL, Turner RM, Veitch GE, Wood A, Zumbrunn C.
    Journal: Chemistry; 2008; 14(34):10683-704. PubMed ID: 18821532.
    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.
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