On the reaction of <i>A</i>-nor-5α-cholestan-2-one with benzeneseleninic anhydride

Abstract

A-Nor-5α-cholestan-2-one (1) was oxidized with BSA under various conditions. The stoichiometric reaction afforded diketones (3 and 4) and α-phenylseleno-ketone (2) while catalytic oxidation with the BSA/PhIO 2 /p-TsOH system resulted in lactones (7a and 7b) and anhydrides (5 and 6). The mechanism of these reactions is discussed. Key words: benzeneseleninic anhydride, A-nor-5α-cholestan-2-one, catalytic oxidation.