Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (2): 464-470.DOI: 10.6023/cjoc201709005 Previous Articles     Next Articles



郑修文a,b, 马海燕a, 丁凯b   

  1. a 华东理工大学化学与分子工程学院 金属有机化学研究室 上海 200237;
    b 中国科学院上海有机化学研究所 天然产物合成重点实验室 上海 200032
  • 收稿日期:2017-09-05 修回日期:2017-10-11 发布日期:2017-10-16
  • 通讯作者: 马海燕, 丁凯;

Practical Syntheses of Equilin and Its Derivatives

Zheng Xiuwena,b, Ma Haiyana, Ding Kaib   

  1. a Laboratory of Organometallic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237;
    b CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2017-09-05 Revised:2017-10-11 Published:2017-10-16
  • Contact: 10.6023/cjoc201709005;

Equilin and its derivatives are important active ingredients of conjugated estrogens, extracted from pregnant horse urine. However, they are still challenge synthetic targets due to the presence of an unstable non-conjugated double bond. Equilin (7), 17β-dihydroequilin (8) and 17α-dihydroequilin (9) were efficiently synthesized from commercially available 19-hydroxyandrost-4-ene-3, 17-dione via retro-aldol aromatization with the overall yields of 32%, 37% and 25%, respectively.

Key words: equilin, conjugated estrogen, aromatization, steroid