Stereo-controlled synthesis of prostaglandin synthons

Abstract

Novel cyclopentanoid precursors [(±)-c-2-cyanomethyl-t-3-methoxymethylcyclopentane-r-1,c-4-diyl diacetate (22) and (±)-c-2-cyanomethyl-t-3-triphenylmethoxymethylcyclopentane-r-1,c-4-diyl diacetate (34)] for the prostanoids have been prepared by oxidative cleavage of 5,6-bisalkoxymethylnorbornenes [(11b) and (26)], and their utility has been demonstrated by conversion into known lactone intermediates [(25) and (35)] for prostaglandin synthesis.