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Citation: Xie Xiantao, Jin Yu, Xu Sheng, Ding Kai. Efficient Synthesis of 6-Substitued-3-aminoestrogens[J]. Chinese Journal of Organic Chemistry, ;2017, 37(3): 767-772. doi: 10.6023/cjoc201610005 shu

Efficient Synthesis of 6-Substitued-3-aminoestrogens

Xie Xiantao ^a ,
Jin Yu ^b ,
Xu Sheng ^a,*,, ,
Ding Kai ^c,*,,

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

Corresponding author: Xu Sheng, xusheng@ecust.edu.cn Ding Kai, dingkai@mail.sioc.ac.cn
Received Date: 4 October 2016
Revised Date: 8 November 2016

Fund Project: the National Natural Science Foundation of China 20902098the National Natural Science Foundation of China U1362111

Figures(5)

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.
- estrogen,
- enamination,
- aromatization,
- intramolecular nucleophilic addition
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