Construction of Morphan Derivatives by Nitroso-Ene Cyclization:   Mechanistic Insight and Total Synthesis of (+/-)-Kopsone

doi:10.1002/anie.201706018

CORC > 北京大学 > 化学与分子工程学院

	Construction of Morphan Derivatives by Nitroso-Ene Cyclization: Mechanistic Insight and Total Synthesis of (+/-)-Kopsone
	Zhai, Li ; Tian, Xuechao ; Wang, Chao ; Cui, Qi ; Li, Wenhua ; Huang, Sha-Hua ; Yu, Zhi-Xiang ; Hong, Ran
刊名	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
	2017
关键词	alkaloids cyclization diradicals morphan core nitroso-ene reactions ORGANIC-SYNTHESIS CYCLOHEXANONES ALKALOIDS GENERATION ESTERS
DOI	10.1002/anie.201706018
英文摘要	A type II nitroso-ene cyclization was developed for the construction of morphan derivatives with good functional-group tolerance. DFT calculations revealed that the nitrosoene reaction proceeds in a stepwise manner involving diradical or zwitterionic intermediates. The rate-determining step is C-N bond formation, followed by a rapid hydrogen-transfer step with a chair-conformation transition state. The current approach was also successfully applied in the first total synthesis of (+/-)-kopsone, a highly strained yet simple morphan-type alkaloid isolated from Kopsia macrophylla.; National Natural Science Foundation of China [21672236, 21290184, 21402121, 21232001]; Strategic Priority Research Program [XDB20000000]; Key Research Program of Frontier Sciences of the Chinese Academy of Sciences [QYZDY-SSW-SLH026]; Shanghai Science and Technology Commission [15JC1400400]; Shanghai Institute of Technology [XTCX2015-16]; SCI(E); ARTICLE; 38; 11599-11603; 56
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/470899]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Zhai, Li,Tian, Xuechao,Wang, Chao,et al. Construction of Morphan Derivatives by Nitroso-Ene Cyclization: Mechanistic Insight and Total Synthesis of (+/-)-Kopsone[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2017.
APA	Zhai, Li.,Tian, Xuechao.,Wang, Chao.,Cui, Qi.,Li, Wenhua.,...&Hong, Ran.(2017).Construction of Morphan Derivatives by Nitroso-Ene Cyclization: Mechanistic Insight and Total Synthesis of (+/-)-Kopsone.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION.
MLA	Zhai, Li,et al."Construction of Morphan Derivatives by Nitroso-Ene Cyclization: Mechanistic Insight and Total Synthesis of (+/-)-Kopsone".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017).