Practical Syntheses of Equilin and Its Derivatives

doi:10.6023/cjoc201709005

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

Articles

马烯雌酮及其衍生物的高效合成

郑修文^a,b, 马海燕^a, 丁凯^b

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 E-mail:haiyanma@ecust.edu.cn;dingkai@mail.sioc.ac.cn

Practical Syntheses of Equilin and Its Derivatives

Zheng Xiuwen^a,b, Ma Haiyan^a, Ding Kai^b

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 E-mail:haiyanma@ecust.edu.cn;dingkai@mail.sioc.ac.cn

1. Practical Syntheses of Equilin and Its Derivatives.PDF(955KB)

Abstract

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

Cite this article

Zheng Xiuwen, Ma Haiyan, Ding Kai. Practical Syntheses of Equilin and Its Derivatives[J]. Chin. J. Org. Chem., 2018, 38(2): 464-470.

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马烯雌酮及其衍生物的高效合成

Practical Syntheses of Equilin and Its Derivatives

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