Threo-(±)-开环异落叶松脂醇二阿魏酸酯的全合成

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.

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

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.