Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 767-772.DOI: 10.6023/cjoc201610005 Previous Articles     Next Articles



谢先涛a, 景羽b, 许胜a, 丁凯c   

  1. a 华东理工大学化学系 上海 200237;
    b 上海师范大学资源化学实验室 上海 200234;
    c 中国科学院上海有机化学研究所 天然产物有机合成化学重点实验室 上海 200032
  • 收稿日期:2016-10-04 修回日期:2016-11-08 发布日期:2016-11-22
  • 通讯作者: 许胜,;丁凯,;
  • 基金资助:


Efficient Synthesis of 6-Substitued-3-aminoestrogens

Xie Xiantaoa, Jin Yub, Xu Shenga, Ding Kaic   

  1. a Department of Chemistry, East China University of Science and Technology, Shanghai 200237;
    b Laboratory of Resource Chemistry, Shanghai Normal University, Shanghai 200234;
    c CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2016-10-04 Revised:2016-11-08 Published:2016-11-22
  • Contact: 10.6023/cjoc201610005;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 20902098, U1362111).

3-Aminoestrogens are promising estrogen drugs. Traditional synthesis of the estrogens used estrone as a raw material, however, was not suitable for diversity-oriented synthesis. Herein, an efficient synthesis of 6-substitued-3-aminoestrogens from easily available 19-hydroxy-androst-4-ene-3,17-dione via a tandem retro-aldol aromatization/intermolecular nucleophilic addition is presented. The method featured easily available reagents, simple operation and introduction of two substituents in one step.

Key words: estrogen, enamination, aromatization, intramolecular nucleophilic addition