3β-羟基雄甾-4-烯-6,17-二酮的合成

Synthesis of 3β-Hydroxyandrost-4-en-6,17-dione

去氢表雄酮醋酸酯经过氧甲酸环氧化、高碘酸开环、IBX氧化、脱水和碱性水解等5步反应,以55%的总收率合成得到了非雄性激素芳香化酶抑制剂3β-羟基雄甾-4-烯-6,17-二酮。在环氧化反应中,利用价廉、易制备的过氧甲酸以几乎定量的收率得到了环氧化合物。使用IBX氧化邻二醇,以98.5%的收率得到氧化产物,避免了使用处理困难并且污染环境的铬试剂。

3β-Hydroxyandrost-4-en-6, 17-dione （3-OHAT）, a non-androgenic aromatase inhibitor, was synthesized via a new process. With dehydroepiandrosterone acetate as starting material, the synthetic procedure included five steps： epoxidation of C=C bond with performic acid, ring opening of the epoxide with periodic acid, oxidation of 6-hydroxy by IBX, elimination of H2O and hydrolysis of the ester. The total yield was up to 55 %. The use of performie acid, an affordable and easily prepared reagent, in epoxidation led to quantitatively the target epoxide. The oxidation of the 1,2-diol by IBX provided the oxidative product with a high yield of 98.5% , moreover, the introduction of IBX avoided the use of chromic reagent, which leads to the tedious work-up for the product purification and environmental pollution.