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(—)-牛蒡苷元及其对映异构体的不对称合成新方法 被引量:1

A New Method for Asymmetric Synthesis of (—)-Arctigenin and Its Enantiomer
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摘要 (—)-牛蒡苷元属于二苄基丁内酯型木脂素,是中药牛蒡子的主要活性成分.为了研究牛蒡苷元的构效关系,报道了(—)-牛蒡苷元及其对映异构体的不对称合成新方法.以苯丙酸衍生物为起始原料,首先利用噁唑烷酮类手性辅基构建丁内酯β位的手性中心,R构型和S构型β-苄基丁内酯的ee值分别为98%和96%.再利用空间位阻效应在α位构建第二个手性中心,最后脱除保护基得到目标产物.经6步反应,分别以58%、55%的总收率和97%、96%的ee值得到(—)-牛蒡苷元和(+)-牛蒡苷元.为接下来拟进行的结构优化奠定了技术基础. (—)-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 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 (—)-arctigenin and (+)-arctigenin with 97% and 96% ee, respectively. This work paved the way for further structural optimization of arctigenin.
出处 《有机化学》 SCIE CAS CSCD 北大核心 2016年第5期1111-1117,共7页 Chinese Journal of Organic Chemistry
基金 国家自然科学基金(No.30873437) 国家教育部博士点基金(No.20112133110001)资助项目~~
关键词 牛蒡苷元 噁唑烷酮 EVANS 木脂素 丁内酯 不对称合成 arctigenin oxazolidinone Evans lignan butyrolactone asymmetric synthesis
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参考文献27

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二级参考文献5

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