A seven-stage stereospecific synthesis of the natural phytosteroid "chiogralactone" has been effected from the readily available 3β, 16α-diacetoxypregn-5-en-20-one. The scheme of the synthesis includes the Reformatskii reaction with this 20-ketone, the hydrogenation of the δ-lactone formed to the 21α(CH3) saturated lactone, the opening of the ring and the saponification of the 3-acetoxy group, the conversion of the latter into the 3,16α-ditosylate, and the alkaline treatment of the ditosylate, leading to a 3,5α-cyclosteroid with a δ-lactone ring and the α(H) configuration of the C(16) center. This is the key stage of the synthesis. Subsequent transformations — the oxidation of the 6-hydroxy group to a 6-keto group, the opening of the cyclopropane ring, and saponification of the 3-acetoxy group — led to the 23 → 16 lactone of 3β, 16β-dihydroxy-6-oxo-24-nor-5α-cholan-23-oic acid, which was identical, according to literature characteristics, with "chiogralactone." Another way of approach to its 3,6-dihydroxy analog was studied on the basis of 5,6α:16,17α-diepoxysteroids. It was shown that on both Pd and Pt catalysts hydrogenolysis takes place primarily of the 16,17α-oxide ring.