Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol

doi:10.1039/c7qo00654c

	Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol
	Gu, Yueqing 1; Huang, Jun 1; Gong, Jianxian 1; Yang, Zhen 1,2,3
刊名	ORGANIC CHEMISTRY FRONTIERS
	2017-12-01
卷号	4 期号:12 页码:2296-2300
ISSN号	2052-4129
DOI	10.1039/c7qo00654c
文献子类	Article
英文摘要	The total synthesis of orientalol F has been achieved starting from 1,4-dioxaspirodecan-8-one 11 in 13 steps. The key steps in this synthesis feature: (1) gold-catalyzed tandem cycloisomerization of alkynediol 10 for the formation of its seven-membered oxa-bridged bicyclic skeleton 9 of orientalol F, (2) visible-light-promoted organocatalytic aerobic oxidation of silyl enol ether 16 to enone 17, (3) Barbier-type butenylation for the diastereoselective synthesis of allylic alcohol 18 from enone 17, and (4) substrate-controlled Pd-catalyzed hydrogenation of 20 for the stereoselective installation of the C1 stereogenic center of 8.
WOS关键词	4+3 CYCLOADDITION REACTION ; FORMAL SYNTHESIS ; CARBONYL YLIDE ; GUAIANE SESQUITERPENE ; BIOLOGICAL EVALUATION ; RING-SYSTEM ; (-)-ENGLERIN ; ENGLERIN ; PLATINUM ; OXIDATION
WOS研究方向	Chemistry
语种	英语
出版者	ROYAL SOC CHEMISTRY
WOS记录号	WOS:000416065700002
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/168328]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者	Yang, Zhen
作者单位	1.Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China 2.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing Natl Lab Mol Sci,Coll Chem & Mol Engn, Beijing 100871, Peoples R China 3.Peking Univ, Peking Tsing Hua Ctr Life Sci, Beijing 100871, Peoples R China
推荐引用方式 GB/T 7714	Gu, Yueqing,Huang, Jun,Gong, Jianxian,et al. Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol[J]. ORGANIC CHEMISTRY FRONTIERS,2017,4(12):2296-2300.
APA	Gu, Yueqing,Huang, Jun,Gong, Jianxian,&Yang, Zhen.(2017).Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol.ORGANIC CHEMISTRY FRONTIERS,4(12),2296-2300.
MLA	Gu, Yueqing,et al."Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol".ORGANIC CHEMISTRY FRONTIERS 4.12(2017):2296-2300.