Efficient oxidative radical cyclizations of ester enolates with carbocation desilylation as termination: synthesis of cyclopentanoid monoterpenes and analogues.
[reaction: see text] An efficient oxidative radical cyclization approach for the synthesis of 2-alkenyl cyclopentane or cyclohexane carboxylates from omega-silylallyl ester enolates induced by recyclable SET oxidant ferrocenium hexafluorophosphate has been developed. A new tandem alkoxycarbonylation/oxidative radical cyclization/cationic termination process forms the basis for a five-step synthesis of the cyclopentanoid monoterpene dihydronepetalactone and analogues.
Jahn
Ullrich
U
Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany. u.jahn@tu-bs.de
Hartmann
Philip
P
Kaasalainen
Emmi
E