Stereoselective Synthesis of Medium-Sized Carbocycles Using Alkoxy Radical Fragmentation as a Key Methodology

Abstract

Stereoselective and regioselective synthesis of functionalized seven- and eight-membered carbocyclic systems was achieved by the ring expansion-cleavage of readily prepared [3.2.1] and [3.3.1] bicyclic alcohols using alkoxy radical fragmentation at room temperature. Transannular migration in the cyclooctane ­system explain formation of unusual products.