959923-25-2Relevant academic research and scientific papers
Synthesis of natural products from the Indian neem tree Azadirachta indica
Veitch, Gemma E.,Pinto, Andrea,Boyer, Alistair,Beckmann, Edith,Anderson, James C.,Ley, Steven V.
, p. 569 - 572 (2008)
The synthesis of five natural products (3, 6, 7, 10, and 14), isolated from the Indian neem tree Azadirachta indica, is reported from a common intermediate (2). The judicious choice of transacetalization conditions allows efficient access to both the azadirachtinin (9 and 10) and the azadirachtin (3, 6, 7, and 14) skeletons
The synthesis of azadirachtin: A potent insect antifeedant
Ley, Steven V.,Abad-Somovilla, Antonio,Anderson, James C.,Ayats, Carles,Baenteli, 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.,Goebel, 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
experimental part, p. 10683 - 10704 (2009/12/31)
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.
A relay route for the synthesis of azadirachtin
Veitch, Gemma E.,Beckmann, Edith,Burke, Brenda J.,Boyer, Alistair,Ayats, Carles,Ley, Steven V.
, p. 7633 - 7635 (2008/09/19)
(Chemical Equation Presented) 22 Years in the making: Azadirachtin (1) was synthesized for the first time by a highly convergent approach, utilizing a Claisen rearrangement and a radical cyclization as key steps. End-game strategies relied on intermediate 2, which could be obtained by synthetic methods as well as by degradation of 1. Bn = benzyl, TBS = tert- butyldimethylsilyl.
