吲哚生物碱Arborisidine和Subincanadine C的合成研究

发布时间：2018-03-10 06:22

本文选题：Arborisidine　切入点：Subincanadine　出处：《兰州大学》2017年硕士论文　论文类型：学位论文

【摘要】：本论文主要包括以下的三个部分:(1)单萜类吲哚生物碱综述;(2)Arborisidine的合成研究;(3)Subincanadine C的合成研究。第一部分:单萜类吲哚生物碱的分类、分离、相关化合物的生理活性以及代表性化合物的合成方法的综述。第二部分:以色胺和2,3-戊二酮为起始原料,经过Pictet Spengler反应,活泼氢存在下的Grignard加成反应,aza-Cope/Mannich重排反应,成功地得到了关键四环中间体2-91,随后希望采用马大为教授发展的碘参与的氧化偶联反应得到最终的天然产物Arborisidine,现在这一部分的工作还在进一步的探究之中。第三部分:受到了上一部分工作的启发,我们又对季铵盐类吲哚生物碱Subincanadine C进行了合成研究。最初的尝试是从中间体2-91’出发,但是由于后期某些反应的失败,所以对合成顺序进行了调整。使用2,3-丁二酮替换2,3-戊二酮作为起始原料,采用同样的策略构筑关键四环中间体3-43,然后通过Rubottom氧化反应在羰基的α位氧化出一个羟基,希望再经过Wittig反应得到关环前体,并最终通过SN2反应完成天然产物Subincanadine C的全合成,目前这一部分工作还在进行之中。
[Abstract]:This thesis mainly includes the following three parts: 1) Review of the synthesis of monoterpene indole-like alkaloids; Synthesis of Arborisidine; Synthesis of Subincanadine C. part one: classification and Separation of Monoterpene Indole Alkaloids, Arborisidine and Arborisidine. A review of the physiological activities of related compounds and the synthesis of representative compounds. Part two: the Grignard addition reaction in the presence of active hydrogen by using tryptamine and 2-tri-pentanedione as starting materials, and the Grignard addition reaction in the presence of active hydrogen. The key quarter-ring intermediate 2-91was successfully obtained, and then the final natural product Arborisidine was obtained by using the oxidative coupling reaction developed by Professor MaDawei. The third part of the work is still in the process of further exploration. Part: inspired by the previous work, We also studied the synthesis of Subincanadine C, an indole alkaloid of quaternary ammonium salts. The initial attempt was based on the intermediate 2-91', but due to the failure of some late reactions, Therefore, the synthesis order was adjusted. The key four-ring intermediates, 3-43, were constructed using the same strategy as the starting material, and then a hydroxyl group was oxidized at the 伪 position of carbonyl group by Rubottom oxidation reaction. It is hoped that the closed ring precursor can be obtained by Wittig reaction, and finally the natural product Subincanadine C can be synthesized by SN2 reaction. At present, this part of the work is still in progress.
【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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