中文摘要：

以雌酚酮为原料,以取代的苯甲酰作为雌酚酮酚羟基的保护基,乙二醇为雌酚酮羰基的保护基,经过溴代、脱溴和水解等5步反应,通过优化反应路线、反应试剂及反应条件,以65%的高收率制得3-羟基雌甾-1,3,5（10）,15-四烯-17-酮.中间体及目标产物的结构经过元素分析、核磁共振波谱（NMR）和电喷雾电离-质谱（ESI-MS）确证.

英文摘要：

As an important intermediate, 3-hydroxyestra-1,3,5 （ 10）, 15-tetraene-17-one is widely used in the field of natural product synthesis and drug discovery, especially in the synthesis of estetrol which is produced only by the fetal liver during human pregnancy. In recent years a number of clinical studies have shown that estetrol can be used for perimenopausal syndrome and the replacement of postmenopausal hormone, the pre- vention and treatment of osteoporosis and breast cancer, and the oral contraceptives. Although the synthesis have been reported, low yield and complex purification process are main problems. In order to overcoming the current shortcomings, the development of a new route is necessary. In this paper, estrone was used as starting materials, substituted benzoyl group was applied to protect the phenolic hydroxyl group of estrone and ethane- diol to protect the keto group. Phenyhrimethylammonium tribromide was selected as the optimal brominating re- agent after deep exploration of reaction agents and reaction conditions. Then debromination and hydrolysis re- action was carried out to obtain 3-hydroxyestra-1,3,5 （10）, 15-tetraen-17-one. The total yield of synthetic route was 65% and the purification of the target compound was 99.8% which was confirmed by liguid chroma- tography-mass spectrometry（LC-MS）. The structures of all intermediates and the target compound were con- firmed by elemental analysis, nuclear magnetic resonance （ 1 H NMR, 13 C NMR） and electrospray inoization- mass spectrometry （ESI-MS）.