Carbocyclinone-534及Duotap-520仿生全合成研究

	Carbocyclinone-534及Duotap-520仿生全合成研究; Biomimetic Total Synthesis of (±)-Carbocyclinone-534 and Duotap-520
	曲春雷
导师	邓军
摘要	This paper explains that we have achieved the first biomimetic total synthesis of two novel natural products named carbocyclinone-534 and duotap-520 based on the biomimetic synthesis strategy, and on this basis, we studied the biosynthetic mechanism and revised the biosynthesis of carbocyclinone-534. hypothesis. The thesis specifically includes the following three chapters: In the first chapter, the author mainly summarizes two important C-C bond construction methods in biosynthesis: intramolecular Diels-Alder reaction and phenolic oxidative coupling reaction. The application in the total synthesis of complex natural products is briefly summarized, focusing on the molecular high efficiency and practicality of internal Diels-Alder reaction and phenolic oxidative coupling reaction in the synthesis of complex natural products. In chapter two, the author mainly elaborates the first biomimetic synthesis of carbocyclinone-534 and duotap-520 based on the bio-inspiration strategy. The control of the monomer benzoquinone to different dimerization products is achieved by adjusting the reaction conditions. The key synthesis steps of carbocyclinone-534 include: stereospecific intermolecular Diels-Alder reaction to achieve the dimerization of p-benzoquinone and oxidative dehydrogenation in tandem molecules. The inner Diels-Alder reaction realizes the construction of the key three-membered ring of carbocyclinone-534. Through a series of in-situ control experiments, the synthetic pathways of monomer benzoquinone to carbocyclinone-534 and duotap-520 were studied, which corrected the hypothesis of biogenic synthesis. Finally, starting from the commercially available 1,3,5-trimethoxytoluene, the first biomimetic synthesis of carbocyclinone-534 and duotap-520 was completed in eight steps which was the longest linear step and its biogenic synthesis was corrected. The third chapter is the experimental part of this thesis, which describes in detail the specific operation steps of the important intermediate synthesis experiment and the spectral data of the key intermediate in the thesis.
	2021-05
文献类型	学位论文
条目标识符	http://ir.kib.ac.cn/handle/151853/74490
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	曲春雷. Carbocyclinone-534及Duotap-520仿生全合成研究, Biomimetic Total Synthesis of (±)-Carbocyclinone-534 and Duotap-520[D],2021.

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