促蛋白同化甾体化合物 Ⅲ.乙高诺龙及其4-羟基衍生物的合成

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

摘要: 本文报道了以(±)3-甲氧基-13β-乙基-17(?)-乙炔基甾-2.5(10)-二烯-17-醇为原料,经催化氢化、水解反应制备乙高诺龙的方法。由此法所得产品的熔点、红外及紫外光谱数据与(±)18甲基炔诺酮经催化氨化制得的乙高诺龙完全一致。本文还从(±)13β-乙基-17β-羟基-5β-甾烷-3-酮经氧化反应合成了4-羟基乙高诺龙,并从元素分析、红外、紫外光谱、质谱以及其双肟衍生物确证了它的结构。

Abstract: 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)