Enantioselective Total Synthesis of (-)-Alstoscholarisine A

doi:10.1021/jacs.6b00625

	Enantioselective Total Synthesis of (-)-Alstoscholarisine A
	Liang, Xiao 1,2; Jiang, Shi-Zhi 1; Wei, Kun 1; Yang, Yu-Rong1
	2016-03-02
发表期刊	JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷号	138 期号:8 页码:2560-2562
摘要	We report a concise and highly enantioselective total synthesis of (-)-alstoscholarisine A (1), a recently isolated monoterpenoid indole alkaloid that has significant bioactivity in promoting adult neuronal stem cells proliferation. A highly enantioselective (99% ee), intramolecular Ir-catalyzed Friedel-Crafts alkylation of indole 9 with a secondary allylic alcohol was utilized to establish the first stereogenic center upon which the other three contiguous chiral centers were readily set by a highly stereoselective tandem 1,4-addition and aldol reaction. The key tetrahydropyran was constructed through a hemiacetal reduction, and the final aminal bridge was forged by a one-pot reductive amination/cyclization. The conciseness of this approach was highlighted by building core bonds in each step with a minimalist protecting group strategy.
DOI	10.1021/jacs.6b00625
收录类别	SCI
语种	英语
WOS记录号	WOS:000371453700025
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/26005
专题	植物化学与西部植物资源持续利用国家重点实验室
作者单位	1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
推荐引用方式 GB/T 7714	Liang, Xiao,Jiang, Shi-Zhi,Wei, Kun,et al. Enantioselective Total Synthesis of (-)-Alstoscholarisine A[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2016,138(8):2560-2562.
APA	Liang, Xiao,Jiang, Shi-Zhi,Wei, Kun,&Yang, Yu-Rong.(2016).Enantioselective Total Synthesis of (-)-Alstoscholarisine A.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,138(8),2560-2562.
MLA	Liang, Xiao,et al."Enantioselective Total Synthesis of (-)-Alstoscholarisine A".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 138.8(2016):2560-2562.

条目包含的文件		下载所有文件
文件名称/大小	文献类型	版本类型	开放类型	使用许可
liang201116.pdf（303KB）			开放获取	CC BY-NC-SA	浏览下载