Abstract
Arctigenin, the main active ingredient of traditional chinese medicine (TCM) arctii fructus, belongs to diben- zyl butyrolactone lignans. In order to study the structure-activity relationship of arctigenin, a new method for asymmetric syn- thesis 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 ees of 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
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