1. The reduction of 3-methoxy-D-homoestra-1, 3, 5(10), 8-tetraen-17aβ-ol (IV) with alkali metals in the presence of ammonium chloride or alcohol gives, in addition to 8β, 9α-dihydro derivatives, the 8α, 9α and 8β, 9β-epimers, the structure of which has been shown partly by independent synthesis and partly on the basis of chemical reactions and NMR spectra.
2. Hydrolysis of the reduction products has given 19-nor-D-homotestosterone (III) and its 8α- and 9β, 10α-epimers (V) and (VI). The ketols (III) and (V) readily form hydroperoxides in air.
3. The reduction of the ethylene ketal of 3-methoxy-D-homoestra-1, 3, 5(10), 8-tetraen-17a-one (XIX) takes place stereodirectively and gives only 8β, 9α-dihydro derivatives.