倍半木脂素threo-(±)-3,4-二香草基四氢呋喃阿魏酸酯的全合成  

Total Synthesis of Sesquilignan threo-(±)-3,4-Divanillyltetrahydrofuran Ferulate

作　　者：夏亚穆[1] 毕文慧[1] 王琦[1] 郭英兰[1] 

机构地区：[1]青岛科技大学化工学院,青岛266042

出　　处：《有机化学》2010年第5期684-690,共7页Chinese Journal of Organic Chemistry

基　　金：化学工程山东省强化建设学科开放基金;高等学校博士点专项基金(No2009371920004);山东省泰山学者建设工程基金(No2005011036)资助项目

摘　　要：报道了一条合成天然产物3,4-二香草基四氢呋喃阿魏酸酯的方法.以香草醛为原料,经过两步Stobbe反应构建木脂素骨架,然后再加氢、LiAlH4还原,产物经柱层析分离后得到两个异构体meso-和threo-(±)-开环落叶松脂素;它们分别与TsCl作用,发生分子内反应得到关键的四氢呋喃木脂素中间体meso-和threo-(±)-shonanin;最后,分别与MOM保护的阿魏酸缩合得到倍半木脂素threo-(±)-3,4-二香草基四氢呋喃阿魏酸酯和衍生物erythro-(±)-3,4-二香草基四氢呋喃阿魏酸酯.合成采用汇聚法,经13步,以约8%～9%的总产率得到了目标产物.A method for the synthesis of natural product 3,4-divanillyltetrahydrofuran ferulate was presented. Using vanillina as the material and through two Stobbe reactions to construct the skeleton of lignan （C6-C4-C6）, followed by hydrogenation, LiAlH4 reduction and separation via flash column chromatography, meso- and threo-（ ±）-secoisolarciresinols were obtained. Meso- or threo-（± ）-secoisolarciresinol was reacted with TsCl, respectively, to give the key intermediate meso- or threo-（±）- shonanin, which was then con- densed with ferulaic acid to obtain sesquilignan threo- or its analogue erythro-（±）-3,4-divanillyltetrahydrofuran ferulate. The synthetic method was based on a unified synthetic strategy to obtain target products through 13 steps, in total yield of 8%-9%.

关 键 词：全合成 3 4-二香草基四氢呋喃阿魏酸酯 Stobbe反应 倍半木脂素 

分 类 号：TQ461[化学工程—制药化工]