Highly selective entry to the azadirachtin skeleton via a Claisen rearrangement/radical cyclization sequence.
[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.
Durand-Reville
Thomas
T
Department of Chemistry, Cambridge University, Lensfield Road, Cambridge CB2 1EW, United Kingdom.
Gobbi
Luca B
LB
Gray
Brian Lawrence
BL
Ley
Steven V
SV
Scott
James S
JS