Threo-(±)-开环异落叶松脂醇二阿魏酸酯的全合成

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (5): 947.

Threo-(±)-开环异落叶松脂醇二阿魏酸酯的全合成

夏亚穆, 王伟, 杨丰科, 常亮

青岛科技大学化工学院, 青岛 266042

收稿日期:2009-07-16 出版日期:2010-05-10 发布日期:2010-05-10
通讯作者: 杨丰科, 男, 教授, 主要从事有机合成研究. E-mail: YangFengK@qust.edu.cn
基金资助:
山东省泰山学者基金(批准号: 2005011036)和青岛科技大学化学工程强化建设学科开放基金资助.

Total Synthesis of the Dilignan threo-(±)-Diferuloysecoisolariciresinol

XIA Ya-Mu, WANG Wei, YANG Feng-Ke*, CHANG Liang

College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China

Received:2009-07-16 Online:2010-05-10 Published:2010-05-10
Contact: YANG Feng-Ke. E-mail: YangFengK@qust.edu.cn
Supported by:
山东省泰山学者基金(批准号: 2005011036)和青岛科技大学化学工程强化建设学科开放基金资助.

摘要/Abstract

摘要：

报道了双木脂素threo-(±)-开环异落叶松脂醇二阿魏酸酯的全合成. 以香草醛为原料, 经过两步Stobbe反应构建木脂素骨架, 然后再用LiAlH₄还原、加氢后, 产物经柱层析分离, 得到2个异构体meso-和threo-(±)-开环落叶松脂素; 根据其NMR, IR和HRMS等谱图确认发现, 极性较小的产物threo-(±)-开环落叶松脂素为合成的关键中间体. threo-(±)-开环落叶松脂素与甲氧甲基(MOM)保护的阿魏酸缩合得到目标产物threo-(±)-开环异落叶松脂醇二阿魏酸酯. 合成采用汇聚法, 经11步, 以约8%的总产率得到了目标产物. 该合成方法具有原料价廉易得及操作简便的优点, 并具有一定的实用价值.

关键词: 开环异落叶松脂醇二阿魏酸酯; Stobbe反应; 双木脂素; 全合成

Abstract:

Threo-(±)-diferuloysecoisolariciresinol which belongs to dilignans, has been firstly isolated from the trunk of Machilus thunbergii and exhibits a strong bioactivity. A novel synthetic route to threo-(±)-diferuloysecoisolariciresinol using Vanillina as the starting materials was described. The method involved two Stobbe reactions to construct the skeleton of lignan(C₆—C₄—C₆), followed by LiAlH₄ reduction, hydrogenation to form meso- and threo-(±)-secoisolanciresinol. threo-(±)-Secoisolanciresinol confirmed by NMR, IR and HRMS was the synthetic key intermediate, and then condensated with ferulaic acid to give threo-(±)-diferuloysecoisolariciresinol. The synthesis was based on a unified synthetic strategy to obtain target products through 11 steps, with yield of 8%. The synthetic method has the advantages of easy availability of starting materials, simple operation. So it has considerable practical value.

Key words: Diferuloysecoisolariciresinol; Stobbe reaction; Dilignan; Total synthesis

TrendMD:

夏亚穆, 王伟, 杨丰科, 常亮. Threo-(±)-开环异落叶松脂醇二阿魏酸酯的全合成. 高等学校化学学报, 2010, 31(5): 947.

XIA Ya-Mu, WANG Wei, YANG Feng-Ke*, CHANG Liang. Total Synthesis of the Dilignan threo-(±)-Diferuloysecoisolariciresinol. Chem. J. Chinese Universities, 2010, 31(5): 947.