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Highly selective entry to the azadirachtin skeleton via a Claisen rearrangement/radical cyclization sequence
Thomas Durand-Reville1, Luca B Gobbi, Brian Lawrence Gray
1Department of Chemistry, Cambridge University, Lensfield Road, Cambridge CB2 1EW, United Kingdom.
Organic Letters
|February 26, 2003
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.