本文選題：不對稱合成 + Michael加成��； 參考：《云南大學》2016年碩士論文

【摘要】：Chabamide酰胺生物堿是一個從黑胡椒根中分離出來的酰胺二聚體天然產物分子�；钚匝芯勘砻髟撎烊划a物分子具有較好的抗腫瘤活性及抑制中樞神經系統(tǒng)興奮作用,所以對Chabamide酰胺生物堿進行不對稱合成研究在不對稱合成及醫(yī)藥研發(fā)領域具有重要意義。在C-C鍵的構建中,Michael加成反應是一種重要的合成方法。不對稱Michael加成反應可以用來構建許多天然有機分子及其中間體和藥物分子中的手性中心,且反應條件溫和,構建過程高效、簡潔同時具有較高的選擇性。因此,不對稱Michael加成反應目前已經發(fā)展成為了最有效的化學鍵構建方法之一。本文第一章首先對不對稱Michael加成反應以及Chabamide酰胺生物堿的研究工作進行了綜述性介紹。然后簡介了以有機小分子催化的不對稱Michael加成反應來構筑該天然產物分子中手性中心六元環(huán)的探究,以期能夠完成對該分子的不對稱合成。在手性六元環(huán)的構筑中,文章采用了三種不同的催化模式,分別是基于氫鍵作用的金雞納堿-硫脲催化、基于烯胺作用的金雞納堿-伯胺催化以及基于亞胺離子中間體作用的L-脯氨酸-硅醚催化。經過不對稱Michael加成反應底物的合成以及不對稱催化合成,最終得到了環(huán)合的手性六元環(huán)中間體16'、18和24。為Chabamide酰胺生物堿的不對稱合成打下了基礎,同時也為該類天然產物分子類似物的藥用研究提供了化合物基礎。
[Abstract]:Chabamide amide alkaloid is a natural product molecule of amide dimer isolated from black pepper root.Studies on the activity of the natural product show that the natural product has good antitumor activity and inhibition of central nervous system excitation, so the asymmetric synthesis of Chabamide amide alkaloids is of great significance in the field of asymmetric synthesis and pharmaceutical research and development.Michael addition reaction is an important synthetic method in the construction of C-C bond.Asymmetric Michael addition reaction can be used to construct chiral centers of many natural organic molecules, their intermediates and drug molecules. The reaction conditions are mild, the construction process is efficient, and the process is simple and selective.Therefore, asymmetric Michael addition reaction has been developed as one of the most effective chemical bond construction methods.In the first chapter, the asymmetric Michael addition reaction and the research work of Chabamide amide alkaloids are reviewed.Then the asymmetric Michael addition reaction catalyzed by small organic molecules was briefly introduced to construct the chiral central six-member ring in the natural product molecule in order to complete the asymmetric synthesis of the molecule.In the construction of chiral six-member ring, three different catalytic modes were used in this paper.The catalytic activity of cinchona alkaloid-primary amine based on enamine and L-proline-silica ether catalyst based on the intermediate of imine ion.After the synthesis of asymmetric Michael addition substrates and asymmetric catalytic synthesis, the chiral chiral hexagonal intermediates of 16 ~ (18) and 24 ~ (th) were obtained.It lays a foundation for the asymmetric synthesis of Chabamide amide alkaloids, and also provides the basis for the medicinal research of this kind of natural product molecular analogues.
【學位授予單位】：云南大學
【學位級別】：碩士
【學位授予年份】：2016
【分類號】：O629.3

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