Efficient Synthesis of 6-Substitued-3-aminoestrogens

doi:10.6023/cjoc201610005

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

Notes

6-取代-3-胺基雌激素的高效合成

谢先涛^a, 景羽^b, 许胜^a, 丁凯^c

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,E-mail:xusheng@ecust.edu.cn;丁凯,E-mail:dingkai@mail.sioc.ac.cn E-mail:xusheng@ecust.edu.cn;dingkai@mail.sioc.ac.cn
基金资助:
国家自然科学基金（Nos.20902098，U1362111）资助项目.

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

Received:2016-10-04 Revised:2016-11-08 Published:2016-11-22
Contact: 10.6023/cjoc201610005 E-mail:xusheng@ecust.edu.cn;dingkai@mail.sioc.ac.cn
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

Cite this article

Xie Xiantao, Jin Yu, Xu Sheng, Ding Kai. Efficient Synthesis of 6-Substitued-3-aminoestrogens[J]. Chin. J. Org. Chem., 2017, 37(3): 767-772.

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6-取代-3-胺基雌激素的高效合成

Efficient Synthesis of 6-Substitued-3-aminoestrogens

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