Radical Cyclization of (Bromomethyl)dimethylsilyl Propargyl Ethers; VI. Serial Radical Cyclizations Leading to a Stereoselective Synthesis of Functionalized Diquinane Framework from an Acyclic Substrate¹

Abstract

Radical cyclization of 4-[(bromomethyl)dimethyl-siloxy)-2-methyl-1-undecene-5-yne in the presence of acrylonitrile leads stereoselectively by a radical reaction cascade to the diquinane system. This one-pot reaction allows the consecutive formation of four carbon-carbon bonds, with two contiguous quaternary centers and controls the stereoselective construction of four stereogenic centers.