Citation: Wu Ping, Xu Kai, Fu Ying, Kang Tingguo, Dou Deqiang, Zhai Yanjun. A New Method for Asymmetric Synthesis of (－)-Arctigenin and Its Enantiomer[J]. Chinese Journal of Organic Chemistry, ;2016, 36(5): 1111-1117. doi: 10.6023/cjoc201511040 shu

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

1.
School of Pharmacy, Liaoning University of Traditional Chinese Medicine, Dalian 116600

Corresponding author: Zhai Yanjun, wupingtcm@163.com
Received Date: 19 November 2015
Revised Date: 21 December 2015

Fund Project: Project supported by the National Natural Science Foundation of China No.30873437and the Ph.D. Program Foundation of the Ministry of Education of China No.20112133110001

Figures(5)

(－)-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.
- arctigenin,
- oxazolidinone,
- Evans,
- lignan,
- butyrolactone,
- asymmetric synthesis
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沈阳化工大学材料科学与工程学院沈阳 110142