Mansonone D的全合成

发布时间：2018-03-10 05:18

本文选题：Pechmann缩合反应　切入点：碳正离子重排　出处：《郑州大学》2017年硕士论文　论文类型：学位论文

【摘要】：我们课题组在合成taiwaniaquinoids的过程中,应用了香豆素的形成--水解加氢顺序将必需的异丙基侧链引入到芳环上。但是在我们最初尝试通过使用四氢芴衍生物1作为底物的Pechmann缩合反应形成关键香豆素时发生了意想不到的碳正离子重排反应,最终形成化合物2,在本论文第一部分我们将对这种重排的机理做一些简单的探究。我们在本论文的第二部分完成Mansonone D天然产物的全合成中同样也应用到Pechmann缩合反应,高效地在3-甲基邻苯二酚的6-位引入顺式的烯烃支链,为后面构建萘环骨架提供了构型一致的顺式结构。我们在完成Mansonone D的萘环骨架的构建过程中应用到构建电环化底物的亲核反应和碳酸铯催化下的电环化反应,此方法可以在有机合成化学中作为构建芳香环构建的有效参考。我们以商品化的3-甲基邻苯二酚作为起始原料,通过Pechmann缩合反应、亲核加成、电环化等反应,经过10步完成了Mansonone D的全合成,这条合成路线简洁高效、原子利用率高、经济适用。
[Abstract]:In the process of synthesizing taiwaniaquinoids, The necessary isopropyl side chain was introduced into the aromatic ring by the formation of coumarin-hydrolysate hydrogenation sequence. However, we initially tried to form the key coumarin by Pechmann condensation reaction using tetrahydrofluorene derivative 1 as substrate. An unexpected rearrangement of carbon ions occurs in the prime phase. In the first part of this paper, we will do some simple research on the mechanism of this rearrangement. In the second part of this paper, we will also apply the Pechmann condensation reaction to the complete synthesis of Mansonone D natural products. Highly efficient introduction of cis-alkene branched chains at the 6-site of 3-methyl-catechol, In the process of constructing the naphthalene ring skeleton of Mansonone D, we have used it to construct the nucleophilic reaction of electrocyclized substrate and the electrocyclization reaction catalyzed by cesium carbonate. This method can be used as an effective reference for the construction of aromatic ring in organic synthesis chemistry. We use commercial 3-methyl-catechol as starting material through Pechmann condensation reaction, nucleophilic addition, electrocyclization reaction, etc. The total synthesis of Mansonone D has been completed in 10 steps. This synthesis route is simple and efficient, with high atomic utilization ratio and is economical and applicable.
【学位授予单位】：郑州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.3

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