Threo-(±)-开环异落叶松脂醇二阿魏酸酯的全合成  

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

作　　者：夏亚穆[1] 王伟[1] 杨丰科[1] 常亮[1] 

机构地区：[1]青岛科技大学化工学院,青岛266042

出　　处：《高等学校化学学报》2010年第5期947-952,共6页Chemical Journal of Chinese Universities

基　　金：山东省泰山学者基金(批准号:2005011036);青岛科技大学化学工程强化建设学科开放基金资助

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Sto-bbe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.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.

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 

分 类 号：O625[理学—有机化学]