Multiple Carbon Bond Formation Via the Radical Cyclization of Cycloalkenol Acetals. Application to trans Hydrindan Steroid Precursors

Abstract

The cyclization of the α-iodo mixed acetals derived from properly substituted cyclohexenols , a process which has already been shown to permit the stereoselective and regioselective introduction of a different carbon chain at each of the termini of the allylic double bond, may be used for the construction of trans hydrindans suitable for further elaboration to steroids. In one particular instance, the process involves the formation of four new carbon-carbon bonds in a single operation.