Reactions of 17β-hydroxy-A-norandrost-3(5)-ene-1, 2-dione (Ia) and its 17-propionate (Ib) with several reagents have been examined. Treatment of I with zinc-acetic acid or lithium-liquid ammonia resulted in the reduction of only the C₁-carbonyl group giving 1β, 17β-dihydroxy-A-norandrost-3(5)-en-2-one (II). On the contrary, reaction of I with carbonyl reagents in the usual condition afforded the corresponding derivatives which were condensed at only the C₂-carbonyl group with the reagents. Lithium aluminum hydride or sodium borohydride reduction of I gave the glycols, (IV) and (V), epimeric at C-2 with the 1β-hydroxyl group.