A Facile Synthesis of Optically Pure (-)-(S)-Ipsenol Using a Chiral Titanium Complex

Article abstract of DOI:10.1002/hlca.19900730215

A stereocontrolled synthetic route to optically pure (-)-(S)-ipsenol (I), the pheromone of Pityokteines curvidens and various other bark-beetle species is described.Key step of the synthesis is an enantioselective aldol reaction using a chiral titanium-carbohydrate complex (Scheme 1).The carboxylate function of the optically pure β-hydroxy acid 5 thus obtained in mol quantities is then elaborated to the diene moiety by standard methodology (Scheme 2).