地诺孕素的合成

Synthesis of dienogest

目的研究地诺孕素的合成方法。方法以雌甾-4,9-二烯-3,17-二酮(1)为原料,首先用2,2-二甲基-13,-丙二醇对3位羰基进行保护,再经过环氧化、氰化开环、脱保护制得17α-氰甲基-17β-羟基-13β-甲基甾烷-4,9-二烯-3-酮,即地诺孕素(5)。结果目标化合物结构经1H-NMR1、3C-NMR、MS和IR确证结构,总收率45.5%。结论新工艺原料易得、操作简便、反应条件温和,有一定的工业生产应用价值。

Objective To research the synthetic procedure of dienogest. Methods Dienogest was prepared from estra-4,9-diene-3,17-dione, 2,2-dimethylpropane-1,3-diol via 3-position ketalation, 17-epoxidation, ring cleavage and 3-position hydrolysis reactions. Results The structure of target compound was confirmed by ^1H-NMR, ^13C-NMR, MS and IR. The overall yield was 45.5%. Conclusions The process should have certain value for industrial application considering its availability of the raw materials, simple operation and mild reacting condition.