南方科技大学知识苑(SUSTech KC): Total Synthesis of Astellatol

题名	Total Synthesis of Astellatol
作者	Zhao, Nan1,2 ; Yin, Shuqiang1,2 ; Xie, Shengling1,2 ; Yan, Hao1,2 ; Ren, Pan1,2 ; Chen, Gui1,2 ; Chen, Fang 1,2; Xu, Jing1,2
通讯作者	Xu, Jing
发表日期	2018-03-19
DOI	10.1002/anie.201800167
发表期刊	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 影响因子和分区
ISSN	1433-7851
EISSN	1521-3773
卷号	57 期号:13页码:3386-3390
摘要	A nearly-30-year-old unanswered synthetic puzzle, astellatol, has been solved in an enantiospecific manner. The highly congested pentacyclic skeleton of this rare sesterterpenoid, which possesses a unique bicyclo[4.1.1]octane motif, ten stereocenters, a cyclobutane that contains two quaternary centers, an exo-methylene group, and a sterically encumbered isopropyl trans-hydrindane motif, makes astellatol arguably one of the most challenging targets for sesterterpenoid synthesis. An intramolecular Pauson-Khand reaction was exploited to construct the right-hand side scaffold of this sesterterpenoid. An unprecedented reductive radical 1,6-addition, mediated by SmI2, forged the cyclobutane motif. Last, a strategic oxidation/reduction step provided not only the decisive solution for the remarkably challenging late-stage transformations, but also a highly valuable unravelling of the notorious issue of trans-hydrindane synthesis. Importantly, the synthesis of astellatol showcases a rapid, scalable strategy to access diverse complex isopropyl trans-hydrindane sesterterpenoids.
关键词	cyclizations natural products sesterterpenoids structure elucidation total synthesis
相关链接	[来源记录]
收录类别	SCI ; EI ; IC
语种	英语
重要成果	NI论文
学校署名	第一 ; 通讯
资助项目	SZSTI[CXZZ20150529152325859] ; SZSTI[Ji 20170314]
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000427235600017
出版者	WILEY-V C H VERLAG GMBH
EI入藏号	20181204916494
EI主题词	Scaffolds
EI分类号	Construction Equipment:405.1 ; Chemical Reactions:802.2
ESI学科分类	CHEMISTRY
来源库	Web of Science
引用统计	被引频次[WOS]：57
成果类型	期刊论文
条目标识符	http://sustech.caswiz.com/handle/2SGJ60CL/27922
专题	理学院_化学系深圳格拉布斯研究院
作者单位	1.Southern Univ Sci & Technol, Dept Chem, Shenzhen, Guangdong, Peoples R China 2.Shenzhen Grubbs Inst, Shenzhen, Guangdong, Peoples R China
第一作者单位	化学系
通讯作者单位	化学系
第一作者的第一单位	化学系
推荐引用方式 GB/T 7714	Zhao, Nan,Yin, Shuqiang,Xie, Shengling,et al. Total Synthesis of Astellatol[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2018,57(13):3386-3390.
APA	Zhao, Nan.,Yin, Shuqiang.,Xie, Shengling.,Yan, Hao.,Ren, Pan.,...&Xu, Jing.(2018).Total Synthesis of Astellatol.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,57(13),3386-3390.
MLA	Zhao, Nan,et al."Total Synthesis of Astellatol".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 57.13(2018):3386-3390.