Enantioselective Total Synthesis of (-)-Alstoscholarisine A
Liang, Xiao1,2; Jiang, Shi-Zhi1; Wei, Kun1; Yang, Yu-Rong1
2016-03-02
Source PublicationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume138Issue:8Pages:2560-2562
AbstractWe 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.
DOI10.1021/jacs.6b00625
Indexed BySCI
Language英语
WOS IDWOS:000371453700025
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/26005
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.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
Recommended Citation
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.
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