Rearrangement during attempted allylation of 2α-Bromo-5α-cholestan-3-one

Abstract

Treatment of 2α-bromo-5α-cholestan-3-one with zinc and allyl bromide in benzene-dimethyl sulphoxide yields, amongst other products, the ring-A contracted compounds 2α-(but-3?-en-1?-oyl)-A-nor-5α-cholestane (3) and 2α-[4?-(4?-hydroxyhepta-1?,6?-dienyl)]-A-nor-5α-cholestane (5).*