Preparation and exploitation of chiral cyclopentadienone synthon

Preparation and exploitation of optically pure ketodicyclopentadiene (KDP), carried out by the author's group, is reviewed. Owing to its molecular bias, its alpha,beta-unsaturated ketone functionality, and its facile thermal extrusion of cyclopentadiene, chiral KDP allows stereoselective introduction of both nucleophiles and electrophiles from the convex face and regeneration of the masked double bond to serve itself as a chiral synthon of cyclopentadienone. Potential of KDP has been demonstrated by enantiocontrolled construction of a vareity natural products.