A stereo-controlled total synthesis of dl-prostaglandin F1α (PGF1α) methyl ester (XVIII) and its 15-epimer (XX) starting from 8-oxo-octanenitrile was achieved. This synthesis involved the oxidative cleavage of a bicyclo[2.2.1]heptene (VIII) as a key reaction in order to obtain an appropriate cyclopentane skeleton.
