高收率合成醋酸群勃龙  

Synthesis of Trenbolone Acetate in High Yield

作　　者：张沪跃[1] 陈燕[1] 施蛟[1] 胡欢[1] 

机构地区：[1]复旦大学药学院药物化学教研室,上海200032

出　　处：《复旦学报（医学版）》2002年第3期211-212,共2页Fudan University Journal of Medical Sciences

摘　　要：目的　由雌甾 4,9 二烯 3 ,1 7 二酮 (1 )经五步合成醋酸群勃龙 (6)。方法　雌甾 4,9 二烯 3 ,1 7 二酮(1 )在对甲苯磺酸的催化下与甲醇作用 ,得 3 ,3 二甲氧基 雌甾 5(1 0 ) ,9(1 1 ) 二烯 1 7 酮 (2 ) ,化合物 (2 )用钾硼氢还原 ,得 3 ,3 二甲氧基 雌甾 5(1 0 ) ,9(1 1 ) 二烯 1 7β 醇 (3) ,不经分离 ,用硫酸催化水解 ,得 1 7β 羟基 雌甾 5(1 0 ) ,9(1 1 ) 二烯 3 酮 (4) ,化合物 (4)用DDQ脱氢 ,得 1 7β 羟基 雌甾 4,9,1 1 三烯 3 酮 (群勃龙 ,5) ,再经乙酰化反应 ,得醋酸群勃龙 (6)。总收率为 63 .1 % ,(6)的纯度为 99.6 %。结果　此法以高收率合成了醋酸群勃龙。结论　该合成法具有工业生产价值。Purpose: To prepare trenbolone acetate in five steps from estra-4, 9-diene-3, 17-dione. Methods: Estra-4,9-diene-3,17-dione(1) was treated with methanol in the presenece of p-toluenesulfonic acid to give 3,3-dimethoxy-estra-5(10), 9(11)-dien-17-one(2). And (2) was reduced by potassium borohydride, then hydrolyzed with sulfuric acid gave 17β-hydroxy-estra-5(10), 9(11)-dien-3-one(4), which was dehydrogenated with DDQ to give 17β-hydroxy-estra-4,9,11-trien-3-one(trenbolone, 5), and then, (5) was acetylated to yield trenbolone acetate(6). Total yield of 6 is 63.1% with 99.6% purity. Results: Trenbolone acetate was prepared in high yield. Conclusions: This method is applicable to industrial production.

关 键 词：醋酸群勃龙 脱氢反应 合成 蛋白质同化激素 

分 类 号：R977.13[医药卫生—药品]