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2017 , Vol. 37 >Issue 3: 767 - 772

DOI: https://doi.org/10.6023/cjoc201610005

研究简报

6-取代-3-胺基雌激素的高效合成

  • 谢先涛 ,
  • 景羽 ,
  • 许胜 ,
  • 丁凯
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  • 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

  网络出版日期: 2016-11-22

基金资助

国家自然科学基金（Nos.20902098，U1362111）资助项目.

收起

Efficient Synthesis of 6-Substitued-3-aminoestrogens

  • Xie Xiantao ,
  • Jin Yu ,
  • Xu Sheng ,
  • Ding Kai
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  • 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 date: 2016-10-04

  Revised date: 2016-11-08

  Online published: 2016-11-22

Supported by

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

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摘要

3-胺基雌激素是潜在的雌激素药物，传统的合成方法以雌酚酮为原料，难以进行多样性导向的快速合成.以19-羟基雄甾-4-烯-3，7-二酮为原料，利用串联的retro-aldol芳构化/分子内亲核加成高效合成了6-取代-3-胺基雌激素.该方法试剂易得，操作简单，可一步反应同时导入两个取代基.

关键词： 雌激素; 烯胺化; 芳构化; 分子内亲核加成

本文引用格式

谢先涛 , 景羽 , 许胜 , 丁凯 . 6-取代-3-胺基雌激素的高效合成[J]. 有机化学, 2017 , 37(3) : 767 -772 . DOI: 10.6023/cjoc201610005

Abstract

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

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