Hapalindole-type生物碱、Ferruginene A及 Fennebricin A的不对称合成研究

	Hapalindole-type生物碱、Ferruginene A及 Fennebricin A的不对称合成研究; Study on Asymmetric Syntheses of Hapalindole-type Alkaloids, Ferruginene A and Fennebricin A
	李雪丹
导师	杨玉荣
摘要	Studies on asymmetric syntheses of hapalindole-type alkailoid, ferruginene A and (-)-fennebricin A are described in this thesis, and it includes the following four chapters: In chapter 1, the research progress of iridium-catalyzed enatioselective allylation was reviewed. Iridium-catalyzed allylic alkylation exhibits unique reaction properties in regio- and enantioselectivity, and it is an important method to construct the chiral carbon-carbon bonds and furnish branched products. In the past two decades, allylic ester or secondary allylic alcohol has been used as allylation reagents to carry out asymmetric allyl alkylation with different kinds of nucleophiles under alkalic and acidic conditions respectively, and many remarkable results have been achieved. We found that directly using secondary allylic alcohol as allylation reagents, without further conversion to active ester, has the advantages of step economy and environmental friendliness. The dual catalytic system composed of a chiral Ir/(P, olefin) complex and a chiral amine can control the formation of two chiral centers in one step, meaning important value in the synthesis of natural products and drug molecules. In chapter 2, asymmetric synthesis of hapalindole-type alkaloid was introduced. Hapalindole-type alkaloids are polycyclic indole alkaloids with multiple chiral centers. According to the structure of the polycyclic system, they can be divided into four categories: hapalindoles, fischerindoles, ambiguines, and welwitindolinones. Different structural categories have common structural features. In this chapter, we briefly described the structure, activity, biogenic pathways and total synthesis of this family alkaloids at home and abroad, and selected the representative fischerindole alkaloids with four consecutive chiral centers, (-)-12-epi-fischerindole U isothiocyanate as our target molecule for synthesis research. We used dual catalytic allytion as a key step to furnish products with full control over the configuration of two stereogenic centers, followed by RCM reaction to construct the tricyclic intermediate, and then through the acid catalyzed isopropenyl cyclization in indole C-2, we obtained the core tetracyclic skeleton of fischerindole alkaloids. At the same time, the next work plan is to complete the (-)-12-epi-fischerindole U isothiocyanate total synthesis after a few functional group conversions on the basis of the four-ring skeleton. In chapter 3, asymmetric synthesis of ferruginene A was introduced. Ferruginene A is a new compound isolated by Brigitte Kopp team from the leaves of Rhododendron ferrugineum in 2010, and there has been no report on its total synthesis so far. At the same time, the molecule has five chiral centers, but Brigitte Kopp team only confirmed the absolute configuration of the adjacent four chiral centers, and the absolute configuration of C-5' has been not determined, so we hope to confirm the absolute configuration through total synthesis. Our synthe
	2020-05
文献类型	学位论文
条目标识符	http://ir.kib.ac.cn/handle/151853/74148
专题	昆明植物所硕博研究生毕业学位论文
推荐引用方式 GB/T 7714	李雪丹. Hapalindole-type生物碱、Ferruginene A及 Fennebricin A的不对称合成研究, Study on Asymmetric Syntheses of Hapalindole-type Alkaloids, Ferruginene A and Fennebricin A[D],2020.

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