（毕业设计论文）《broussonetine_D的合成》.doc

毕业论文 题 目 学 院 专 业 班 级 学 生 学 号 指导教师 二〇一一年六月十日Grignard试剂的加成反应，得到羟胺化合物。在合成的过程中，对核磁分析，鉴定了其化学结构，表明所合成产物为目标产物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 摘 要 I ABSTRACT II 目 录 III 1 前言 1 1.1 亚胺糖简介 1 1.2 亚胺糖的生理活性及其医疗应用 1 1.2.1 亚胺糖与糖尿病 1 1.2.2 多羟基生物碱的分类 2 1.3 broussonetines的简介 2 1.4 部分broussonetines的合成 3 1.4.1 broussonetine C的合成 3 1.4.2 broussonetine D和M的合成 4 1.4.3 broussonetine F的合成 6 1.4.4 broussonetine G的合成 7 1.5课题的提出 9 2 实验部分 10 2.1主要仪器 10 2.2主要试剂 10 2.3 broussonetine D的逆合成分析 10 2.4 侧链的合成 11 2.4.1 8-溴代-1-辛醇的制备 11 2.4.2 N-甲基-N-甲氧基-5-羟基戊酰胺的合成 12 2.4.3 8-溴-1-辛醇的羟基TBS保护 12 2.4.4 5-苄氧基-N-甲基-N-甲氧基-5-羟基戊酰胺的合成 12 2.4.5 1-苄氧基-13-叔丁基二甲基硅氧基-十三烷-5酮的制备 13 2.4.6 1-苄氧基-13-((四氢-2H-吡喃-2-)十三烷-5-酮的制备 13 2.4.7 1-(苄氧基)-13-羟基-十三烷-5-酮的制备 14 2.4.8 1-(苄氧基)-13-羟基-十三烷-5-酮的制备 14 2.4.9 1-苄氧基-13-溴-十三烷-5-酮的合成 15 2.4.10 1-苄氧基-13-溴-十三烷-5-酮的羰基保护 15 2.4.11 格式试剂和木糖硝酮的加成反应 15 3 结果与讨论 17 3.1 8-溴-1-辛醇的TBS保护 17 3.2 5-苄氧基-N-甲基-N-甲氧基-5-羟基戊酰胺的合成 17 3.3 1-(苄氧基)-13-羟基-十三