Asymmetric Synthesis of (+)-Hirsutene

Article abstract of DOI:10.1021/jo00238a007

The asymmetric total synthesis of (+)-hirsutene from the regio- and enantioselective 1,4-γ-addition reaction of (-)-(S)-allyl p-tolyl sulfoxide and 2-methyl-2-cyclopentenone is presented.In this total synthesis, a facile ring closure reaction involving enol thioether and enol acetate moieties and the deoxygenation reaction of a highly hindered secondary alcohol via its 2-propanesulfonate were found.An unexpected displacement reaction at the sulfur atom of alkenyl sulfoxides and the addition reactions of the cis sulfinylallyl anions with cyclic enones were also observed during the studies.