Highly selective entry to the azadirachtin skeleton via a Claisen rearrangement/radical cyclization sequence |
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| Authors: | Durand-Reville Thomas Gobbi Luca B Gray Brian Lawrence Ley Steven V Scott James S |
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| Institution: | Department of Chemistry, Cambridge University, Lensfield Road, Cambridge CB2 1EW, United Kingdom. |
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| Abstract: | formula: see text] A highly diastereoselective, microwave-induced Claisen rearrangement of an appropriately substituted propargylic enol ether allows the formation of the sterically congested C8-C14 bond of azadirachtin. When combined with a radical-mediated cyclization of the corresponding allene, this sequence offers rapid entry to the framework of azadirachtin. |
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