（1）苯并异吡喃盐和二苯乙烯衍生物的串联反应研究和（2）生物碱Lycopladine D片断的合成方法研究

发布时间：2018-04-23 18:15

本文选题：苯并异吡喃四氟硼酸盐 + 二苯乙烯衍生物　；参考：《南京大学》2017年硕士论文

【摘要】：本论文包括两个部分的研究内容,一是苯并异吡喃盐和二苯乙烯衍生物的串联反应研究,二是生物碱Lycopladine D片断的合成方法研究。苯并异吡喃四氟硼酸盐(ICTBs)是一类结构特殊的氧杂双烯体,具有非传统的休克尔芳香性且分子整体为缺电子体系。一般而言,苯并异吡喃四氟硼酸盐能够较好地和富电子烯烃发生作用,进而启动串联反应的发生,从而构建出复杂的分子骨架。我们在本工作中发展了苯并异吡喃四氟硼酸盐和富电子二苯乙烯衍生物在乙腈中的新型三组分串联反应,"一锅法"得到了含有苯并菲啶核心骨架的衍生物。该反应由分子间[4+2]环加成引发,再由乙腈对碳正离子中间体亲核进攻,最后由分子内Friedel-Crafts反应终止,连续地构建出多个新的C-C键和C-N键。Lycopladine D是Kobayashi小组2006年从石松科植物地刷子石松中分离得到的一例结构新颖的生物碱,具有独特的多环笼状结构。我们对天然产物Lycopladine D进行了逆合成分析,研究了片断5和50的合成,探索了分子内的关十元环反应、Claisen缩合反应和分子间的格氏反应、亲核反应等一些方法。
[Abstract]:This thesis includes two parts: one is the series reaction of benzo-isopyran salt and stilbene derivative, the other is the synthesis method of alkaloid Lycopladine D fragment. Benzisopyran tetrafluoroborate (ICTBs) is a special type of oxygen heterobenes with unconventional shock aromaticity and an electron-deficient molecular system. In general, benzo-isopyran tetrafluoroborate can interact well with the electron-rich olefins, and then initiate the series reaction, thus the complex molecular framework can be constructed. In this work, we have developed a novel three-component series reaction of benzo-isopyran tetrafluoroborate and electron-rich stilbene derivatives in acetonitrile. The reaction was initiated by intermolecular [42] cycloaddition, then attacked by acetonitrile on the carbon ion intermediate, and finally terminated by intramolecular Friedel-Crafts reaction. Several new C-C bonds and C-N bonds. Lycopladine D were constructed continuously. Lycopladine D was a novel alkaloid isolated from Pinaceae in 2006 by Kobayashi team. It has a unique polycyclic cage structure. The inverse synthesis of natural product Lycopladine D was carried out, the synthesis of fragments 5 and 50 was studied, and some methods such as intermolecular Grignard reaction and nucleophilic reaction were explored.
【学位授予单位】：南京大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.3

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