Monocyclic silyl enol ethers bearing an olefinic and silylacetylenic s
ide chain are irradiated in the presence of the electron transfer sens
itizer 9,10-dicyanoanthracene (DCA) or 1,4-dicyanonaphthaline (DCN). C
yclization of the intermediate silyloxy radical cations efficiently pr
ovides bicyclic and tricyclic ketones with definite regio- and stereoc
hemistry.