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C14 bond in a stereos...

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Veröffentlicht in:	Chemistry : a European journal 2008-11, Vol.14 (34), p.10683-10704
Hauptverfasser:	Ley, Steven V., Abad-Somovilla, Antonio, Anderson, James C., Ayats, Carles, Bänteli, Rolf, Beckmann, Edith, Boyer, Alistair, Brasca, Maria G., Brice, Abigail, Broughton, Howard B., Burke, Brenda J., Cleator, Ed, Craig, Donald, Denholm, Alastair A., Denton, Ross M., Durand-Reville, Thomas, Gobbi, Luca B., Göbel, Michael, Gray, Brian Lawrence, Grossmann, Robert B., Gutteridge, Claire E., Hahn, Norbert, Harding, Sarah L., Jennens, David C., Jennens, Lynn, Lovell, Peter J., Lovell, Helen J., de la Puente, Mary L., Kolb, Hartmuth C., Koot, Win-Jan, Maslen, Sarah L., McCusker, Catherine F., Mattes, Amos, Pape, Andrew R., Pinto, Andrea, Santafianos, Dinos, Scott, James S., Smith, Stephen C., Somers, Andrew Q., Spilling, Christopher D., Stelzer, Frank, Toogood, Peter L., Turner, Richard M., Veitch, Gemma E., Wood, Anthony, Zumbrunn, Cornelia
Format:	Artikel
Sprache:	eng
Schlagworte:	Allene azadirachtin Bonding Claisen rearrangement Decalin epoxidation Insecticides - chemical synthesis Insecticides - chemistry Insects Ketones Limonins - chemical synthesis Limonins - chemistry Molecular Conformation Natural products Stereoisomerism Synthesis Synthesis (chemistry) total synthesis
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