《broussonetine_D的合成》》-毕业论文.doc

PAGE 毕业论文 题 目 broussonetine D的合成 学 院 化学化工学院 专 业 化 学 班 级 化学0702 学 生 学 号 20070204004 指导教师 二〇一一年六月十八日 摘 要 多羟基吡咯生物碱已经从多种植物中分离出，这类化合物具有很好的生物活性，是糖苷酶的有效抑制剂。它们拥有多个羟基的官能团，表现出与单糖的结构类似性，归属于亚胺糖类。在多羟基吡咯生物碱中，broussonetines占据一个特殊的小组，大约拥有30个成员，它们的侧链都含有13个碳链。本文要合成的broussonetine D属于其中之一，首先通过逆合成分析方法，找到了合适的合成路线。本文的工作重点是合成13个碳的侧链，以辛二醇和戊内酯为原料，经过八步反应，完成了侧链的合成。以多羟基环状硝酮作为合成上述天然产物的中间体，通过环状硝酮与13碳链的Grignard试剂的加成反应，得到羟胺化合物。在合成的过程中，对合成出来的每种物质进行核磁分析，鉴定了其化学结构，表明所合成产物为目标产物。 关键词：硝酮; 亚胺糖; 多羟基吡咯碱 ABSTRACT Polyhydroxylated pyrrolidine alkaloids have been isolated from many plants, which show good biological activity because of its inhibition to glycosidases. They have multiple hydroxyl functions and exhibit similar structure with simple sugar, and belong to imino sugar. Broussonetines with a thirteen carbon side chain occupy a special group in imino sugar, which have approximately 30 member. This dissertation described the efforts to synthesize broussonetine D which is among the most active compounds. Firstly, the proper synthetic route was got through the retro-synthetic analysis. Secondly, using1,8-octanediol and δ–valerolactone as raw material, the 13 carbon side chain was completed in eight steps and gram scale. Thirdly, through the addition of thirteen carbons Grignard reagent 010, the precursor for the natural product 011 was obtained. In the process of synthesis, every compound was characterized by NMR analysis . Key words：nitrone；imino sugar；polyhydroxylated pyrrolidine alkaloid 目 录 TOC \o 1-3 \h \u HYPERLINK \l _Toc32341 摘 要 PAGEREF _Toc32341 I HYPERLINK \l _Toc31387 ABSTRACT PAGEREF _Toc31387 II HYPERLINK \l _Toc17163 目 录 PAGEREF _Toc17163 III HYPERLINK \l _Toc18853 1 前言 PAGEREF _Toc18853 1 HYPERLINK \l _Toc3849 1.1 亚胺糖简介 PAGEREF _Toc3849 1 HYPERLINK \l _Toc2164 1.2 亚胺糖的生理活性及其医疗应用 PAGER