Anabolic steroid compounds Ⅲ. Synthesis of norbolethone and its 4-Hydroxy-derivative

Norbolethone was prepared by catalytic hydrogenation of (±)-3-methoxyl-13β-ethyl-17α-ethinyl-2.5(10)-gondien-17β-ol in 40% yield. Its melting point, infrared and ultraviolet spectra were identical with those of product obtained by hydrogenation of (±) -norgestrel. 4-Hydroxynorbolethone was also synthesized from (±)-13β-ethyl-17β-hydroxyl-5β-gona-3-one by oxidation with oxygen in t-BuOK/t-BuOH. Its melting point was 168-170℃. UVλETOH_max 277nm(11.200)