A New Method for Asymmetric Synthesis of (－)-Arctigenin and Its Enantiomer

doi:10.6023/cjoc201511040

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (5): 1111-1117.DOI: 10.6023/cjoc201511040 Previous Articles Next Articles

NOTE

(－)-牛蒡苷元及其对映异构体的不对称合成新方法

吴平, 徐凯, 付莹, 康廷国, 窦德强, 翟延君

辽宁中医药大学药学院大连 116600

收稿日期:2015-11-19 修回日期:2015-12-21 发布日期:2016-01-15
通讯作者: 翟延君 E-mail:wupingtcm@163.com
基金资助:
国家自然科学基金(No.30873437)和国家教育部博士点基金(No.20112133110001)资助项目.

A New Method for Asymmetric Synthesis of (－)-Arctigenin and Its Enantiomer

Wu Ping, Xu Kai, Fu Ying, Kang Tingguo, Dou Deqiang, Zhai Yanjun

School of Pharmacy, Liaoning University of Traditional Chinese Medicine, Dalian 116600

Received:2015-11-19 Revised:2015-12-21 Published:2016-01-15
Supported by:
Project supported by the National Natural Science Foundation of China (No. 30873437) and the Ph.D. Program Foundation of the Ministry of Education of China (No. 20112133110001).

1. A New Method for Asymmetric Synthesis of (－)-Arctigenin and Its Enantiomer.PDF(2985KB)

Abstract

(－)-Arctigenin, the main active ingredient of traditional chinese medicine (TCM) arctii fructus, belongs to dibenzyl butyrolactone lignans. In order to study the structure-activity relationship of arctigenin, a new method for asymmetric synthesis of (－)-arctigenin and its enantiomer was developed. Phenylpropanoic acid derivate was used as starting material and the chiral center of beta butyrolactone was constructed by using oxazolidinone chiral auxiliary. The eesof R and S configurations are 98% and 96%, respectively. Then the second chiral center in the alpha position was constructed benefitting from the steric effect. After removal of protecting group, the target compounds were obtained in 58 % and 55% overall yield of (－)-arcti-genin and (+)-arctigenin with 97% and 96% ee,respectively. This work paved the way for further structural optimization of arctigenin.

Key words: arctigenin, oxazolidinone, Evans, lignan, butyrolactone, asymmetric synthesis

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Wu Ping, Xu Kai, Fu Ying, Kang Tingguo, Dou Deqiang, Zhai Yanjun. A New Method for Asymmetric Synthesis of (－)-Arctigenin and Its Enantiomer[J]. Chin. J. Org. Chem., 2016, 36(5): 1111-1117.

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(－)-牛蒡苷元及其对映异构体的不对称合成新方法

A New Method for Asymmetric Synthesis of (－)-Arctigenin and Its Enantiomer

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