Stereocontrolled synthesis of a prostanoid synthon by oxidative cleavage of substituted norbornene derivatives

Abstract

Novel cyclopentanoid precursors (±)-2α-cyanomethyl-1α,4α-diacetoxy-3β-methoxymethylcyclopentane (21) and (±)-2α-cyanomethyl-1α,4α-diacetoxy-3β-trityloxymethylcyclopentane (25) for the prostanoids have been prepared by oxidative cleavage of substituted norbornene diethers [(4) and (6)], and their utility demonstrated by conversion into the known prostaglandin intermediates (27) and (28).