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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (05): 684-690. 上一篇    下一篇

研究论文

倍半木脂素threo-(±)-3,4-二香草基四氢呋喃阿魏酸酯的全合成

夏亚穆*，毕文慧，王琦，郭英兰   

  1. (青岛科技大学化工学院 青岛 266042)
  • 收稿日期:2009-07-15 修回日期:2009-09-22 发布日期:2009-12-04
  • 通讯作者: 夏亚穆 E-mail:xiaym@qust.edu.cn
  • 基金资助:

    青岛科技大学化学工程重点学科开放基金和山东省自然科学基金(No. Q2006B02)资助项目

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

XIA Ya-Mu, BI Wen-Hui, WANG Qi, GUO Ying-Lan   

  1. (College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042)
  • Received:2009-07-15 Revised:2009-09-22 Published:2009-12-04

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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.

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

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 condensed with ferulaic acid to obtain sesquilignan threo- or its analogue erythro-(±)-3,4-divanillyltetrahy- drofuran ferulate. The synthetic method was based on a unified synthetic strategy to obtain target products through 13 steps, in total yield of 8%～9%.

Key words: total synthesis, 3,4-divanillyltetrahydrofuran ferulate, Stobbe reaction, sesquilignan