Towards a general diastereoselective route to oxabicyclo[3.2.1]octanes   via a gold-catalysed cascade reaction

doi:10.1038/ncomms9617

CORC > 北京大学 > 化学与分子工程学院

	Towards a general diastereoselective route to oxabicyclo[3.2.1]octanes via a gold-catalysed cascade reaction
	Fu, Junkai ; Gu, Yueqing ; Yuan, Hao ; Luo, Tuoping ; Liu, Song ; Lan, Yu ; Gong, Jianxian ; Yang, Zhen
刊名	NATURE COMMUNICATIONS
	2015
关键词	POLARIZABLE CONTINUUM MODEL OXIDATION/1,2-ALKYNYL MIGRATION/CYCLIZATION CASCADE NATURAL-PRODUCT SYNTHESIS ENANTIOSELECTIVE SYNTHESIS STEROIDAL ALKALOIDS SELECTIVE INHIBITOR 4+3 CYCLOADDITIONS PROTON-TRANSFER CORTISTATINS CYCLIZATIONS
DOI	10.1038/ncomms9617
英文摘要	The development of an efficient diastereoselective synthesis of the oxabicyclo[3.2.1]octane ring system bearing two oxygenated quaternary chiral centres represents a significant challenge. This motif can be found in a wide range of natural products with significant biological activities. Here we report the synthesis of such kind of scaffold using a cyclohexane-trans-1,4-diol with an alkyne side chain in the presence of Au(I) catalyst. This is a domino process in which two C-H, two C-O and one C-C bond is assembled through a sequence of cyclization/semi-pinacol rearrangements. This strategy has been successfully applied to the asymmetric formal total synthesis of (+)-cortistatins.; National Science Foundation of China [21372016, 21472006, 21402002]; 863 Program [2013AA092903]; Guangdong Natural Science Foundation [2014A030312004]; NSFC-Shandong Joint Fund for Marine Science Research Centers [U1406402]; Shenzhen Basic Research Program [JCYJ20130329180217059, ZDSYS20140509094114168, JSGG20140717102922014]; SCI(E); PubMed; ARTICLE; lanyu@cqu.edu.cn; gongjx@pku.edu.cn; zyang@pku.edu.cn; 8617; 6
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/417214]
专题	化学与分子工程学院生命科学学院
推荐引用方式 GB/T 7714	Fu, Junkai,Gu, Yueqing,Yuan, Hao,et al. Towards a general diastereoselective route to oxabicyclo[3.2.1]octanes via a gold-catalysed cascade reaction[J]. NATURE COMMUNICATIONS,2015.
APA	Fu, Junkai.,Gu, Yueqing.,Yuan, Hao.,Luo, Tuoping.,Liu, Song.,...&Yang, Zhen.(2015).Towards a general diastereoselective route to oxabicyclo[3.2.1]octanes via a gold-catalysed cascade reaction.NATURE COMMUNICATIONS.
MLA	Fu, Junkai,et al."Towards a general diastereoselective route to oxabicyclo[3.2.1]octanes via a gold-catalysed cascade reaction".NATURE COMMUNICATIONS (2015).