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



吴平, 徐凯, 付莹, 康廷国, 窦德强, 翟延君   

  1. 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
  • 基金资助:


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

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

  1. 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).

(-)-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