天然产物Palhinine A、Strychnochromine和Goniomine的全合成研究

发布时间：2018-06-27 23:39

本文选题：中等环系骨架 + 天然产物　；参考：《兰州大学》2017年博士论文

【摘要】：本论文主要包含有机化合物中中等环系骨架的构筑及其在天然产物全合成中的应用以及对于石松生物碱palhinine A和吲哚生物碱strychnochromine、goniomine的全合成研究,包括以下三章:第一章有机化合物中中等环系骨架的构筑及其在天然产物全合成中的应用(综述)本章按照构环方式的不同简要介绍近些年来关于张力较大的中等环系骨架结构的构筑方法及其在天然产物全合成中的应用。第二章石松生物碱Palhinine A的全合成研究简要介绍了石松生物碱palhinine A的分离、结构特点以及之前的合成尝试,发展了一条以氧化去芳化反应/羟基氧化串联分子内Diels-Alder反应为关键步骤的路线,简洁高效地构筑了palhinine类生物碱中6/6/9三环骨架,实现了这一类分子中张力较大的含氮九元环的构建。第三章吲哚生物碱Strychnochromine和Goniomine的全合成研究简要介绍了吲哚生物碱strychnochromine和goniomine的分离、结构特点及生源合成假说,设计了一条以Michael加成反应和Mitsunobu反应为关键步骤的对于stemmadenine类吲哚生物碱的合成路线,进而完成对于strychnochromine和goniomine的生源合成。利用此策略的合成工作目前仍在进行之中。
[Abstract]:This thesis mainly includes the construction of the intermediate cyclitic framework of organic compounds and its application in the total synthesis of natural products, as well as the total synthesis of palhinine A and strychnochrome goniomine, the alkaloids of Pinus lanceolata and Indole. There are three chapters as follows: the first chapter is the construction of the intermediate cyclists skeleton of organic compounds and its application in the total synthesis of natural products (review). This chapter briefly introduces the high tension of organic compounds in recent years according to the different ways of ring construction. Construction method of isocyclic skeleton structure and its application in total synthesis of natural products. In the second chapter, the total synthesis of palhinine A, an alkaloid of Pinus lanceolata, was briefly introduced, including the isolation, structural characteristics and previous synthesis attempt of the alkaloid Palhinine A. In this paper, a new route is developed, in which oxidative dearomatization / hydroxyl oxidation series intramolecular Diels-Alder reaction is the key step. The tricyclic skeleton of palhinine alkaloids in 6-6-9 is constructed succinctly and efficiently. The construction of nitrogen-containing nine-member ring with high tension in this class of molecules has been realized. In chapter 3, the complete synthesis of indole alkaloids Strychnochromine and Goniomine was introduced. The separation, structure and biosynthesis hypothesis of indole alkaloids strychnochromine and goniomine were briefly introduced. A new route for the synthesis of stemmadenine indole alkaloids was designed with Michael addition reaction and Mitsunobu reaction as the key step, and then the biosynthesis of strychnochromine and goniomine was completed. The synthesis of this strategy is still in progress.
【学位授予单位】：兰州大学
【学位级别】：博士
【学位授予年份】：2017
【分类号】：O629

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