虎皮楠生物碱Daphlongamine E的不对称合成研究

发布时间：2018-06-30 19:40

本文选题：虎皮楠生物碱 + Daphlongamine　；参考：《兰州大学》2017年硕士论文

【摘要】：Daphlongamine E是郝小江小组于2009年从长序虎皮楠叶子中分离得到的一种Calyciphylline A类虎皮楠生物碱。研究表明,Daphlongamine E中含特殊的氮杂[3.3.1]桥环体系和[6/6/5/7/5]五环刚性骨架以及六个手性中心,其复杂的刚性结构使得对它的全合成研究成为一项极具挑战性的工作。在本文中,我们从手性化合物(-)-2-1出发,以金催化烯醇硅醚的环化反应,有机膦催化的[3+2]环加成反应,铱(I)催化的不对称氢化反应,酰基芳酰基过氧化物的重排反应以及分子内的aldol反应为关键步,总共17步完成了Daphlongamine E的不对称五环骨架的构建,为Daphlongamine E的不对称全合成奠定了基础。
[Abstract]:Daphlongamine E is a Calyciphylline A alkaloid isolated from the leaves of Cymbidium longensis by Hao Xiaojiang team in 2009. It is shown that Daphlongamine E contains a special [3.3.1] bridged ring system and [6 / 6 / 5 / 7 / 5] pentacyclic rigid skeleton and six chiral centers. Its complex rigid structure makes it a challenging task to study its full synthesis. In this paper, starting from chiral compound (-) -2-1, we use gold to catalyze the cyclization of enol silyl ether, [32] cycloaddition reaction catalyzed by organic phosphine, and asymmetric hydrogenation reaction catalyzed by iridium (I). The rearrangement of acyl aryl peroxide and the intramolecular aldol reaction were the key steps. The asymmetric pentacyclic skeleton of Daphlongamine E was constructed in 17 steps, which laid the foundation for asymmetric synthesis of Daphlongamine E.
【学位授予单位】：兰州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O629.3

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