Asymmetric total synthesis of (-)-lingzhiol via a Rh-catalysed [3+2]   cycloaddition

doi:10.1038/ncomms6707

CORC > 北京大学 > 化学与分子工程学院

	Asymmetric total synthesis of (-)-lingzhiol via a Rh-catalysed [3+2] cycloaddition
	Long, Rong ; Huang, Jun ; Shao, Wenbin ; Liu, Song ; Lan, Yu ; Gong, Jianxian ; Yang, Zhen
刊名	nature communications
	2014
关键词	CARBON QUATERNARY STEREOCENTERS ELECTRON-DEFICIENT OLEFINS DOUBLE MICHAEL ADDITION ENANTIOSELECTIVE CONSTRUCTION FUNCTIONALIZED CYCLOPENTENES CYCLOTRYPTAMINE ALKALOIDS CONJUGATE ADDITION PALLADIUM ACID ALLENES
DOI	10.1038/ncomms6707
英文摘要	The development of efficient reactions for the one-pot construction of bicyclic ring systems bearing two quaternary carbon centres at their bridgehead positions represents a significant challenge to synthetic chemistry. The development of new methods capable of overcoming this challenge is highly desirable, because this motif can be found in a wide range of natural products with significant biological activities. Herein, we report an efficient [3+2] cycloaddition reaction between an enal and an alleno rhodium species, which was generated in situ from the corresponding enynol via a retro metal-propargylation reaction, to give [3.3.0] and [3.4.0] bicyclic systems bearing two quaternary atoms at their bridgehead positions. The developed chemistry has been successfully applied to the asymmetric total synthesis of natural product (-)-lingzhiol (4) for the first time in 17 steps.; http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000347229300003&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=8e1609b174ce4e31116a60747a720701 ; Multidisciplinary Sciences; SCI(E); PubMed; 16; ARTICLE; lanyu@cqu.edu.cn; gongjx@pku.edu.cn; zyang@pku.edu.cn; 5707; 5
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/327093]
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	Long, Rong,Huang, Jun,Shao, Wenbin,et al. Asymmetric total synthesis of (-)-lingzhiol via a Rh-catalysed [3+2] cycloaddition[J]. nature communications,2014.
APA	Long, Rong.,Huang, Jun.,Shao, Wenbin.,Liu, Song.,Lan, Yu.,...&Yang, Zhen.(2014).Asymmetric total synthesis of (-)-lingzhiol via a Rh-catalysed [3+2] cycloaddition.nature communications.
MLA	Long, Rong,et al."Asymmetric total synthesis of (-)-lingzhiol via a Rh-catalysed [3+2] cycloaddition".nature communications (2014).