Cu催化对苯醌分子间[5+2]环化二聚反应及其在(—)—perezoperezone全合成中的应用研究

	Cu催化对苯醌分子间[5+2]环化二聚反应及其在(—)—perezoperezone全合成中的应用研究; Cu catalyzed intermolecular [5+2] cyclization dimerization of p-benzoquinone and its application in total synthesis of (–)-perezoperezone
	吴海
导师	邓军
摘要	This thesis described a method for the synthesis of bicyclic[3,2,1]octadienone skeleton based on CuI-catalyzed intermolecular [5+2] cycloaddition reaction of hydroxyp-benzoquinone and the first total synthesis of (?)-perezoperezone by using this methodology. This thesis consists of the following three chapters: The first chapter summarized the research progress of [5+2] cycloaddition reactions. We sumerized different types of [5+2] cycloaddition reactions and their application in the total synthesis of natural products. The second chapter discussed our development of the homodimerization of p-quinone and it’s application in the total synthesis of (?)-perezoperezone. Inspired by our previous total synthesis of asperchalasine A through [5+2] heterodimerizatio of o-quinone and double bond and the possible biosynthetic pathway of (?)-perezoperezone, we developed a CuI catalyzed intermolecular [5+2] cycloaddition reaction of hydroxy p-benzoquinone. More than 36 bicyclo[3,2,1]octadienones were prepared by using this method in typically good yields and excellent diastereoselectivities. Applying this synthetic approach enabled a concise nine-step total synthesis of (?)-perezoperezone from commercially available 3, 5-dimethoxytoluene. The third chapter is the experimental part, which describes the experimental procedures about the syntheses of important compounds in the thesis and the spectral data of key intermediates.
	2020-05
文献类型	学位论文
条目标识符	http://ir.kib.ac.cn/handle/151853/74191
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	吴海. Cu催化对苯醌分子间[5+2]环化二聚反应及其在(—)—perezoperezone全合成中的应用研究, Cu catalyzed intermolecular [5+2] cyclization dimerization of p-benzoquinone and its application in total synthesis of (–)-perezoperezone[D],2020.

条目包含的文件
文件名称/大小	文献类型	版本类型	开放类型	使用许可
吴海-吴海-硕士学位论文608e6375（7298KB）	学位论文		限制开放	CC BY-NC-SA	请求全文