Enantioselective Total Synthesis of (-)-Alstoscholarisine A | |
Liang, Xiao1,2; Jiang, Shi-Zhi1; Wei, Kun1; Yang, Yu-Rong1![]() | |
刊名 | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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2016-03-02 | |
卷号 | 138期号:8页码:2560-2562 |
英文摘要 | 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. |
类目[WOS] | Chemistry, Multidisciplinary |
研究领域[WOS] | Chemistry |
关键词[WOS] | CELL FATE ; ALLYLATION ; ALKALOIDS ; CATALYSIS ; CYCLIZATIONS ; ALCOHOLS |
收录类别 | SCI |
语种 | 英语 |
WOS记录号 | WOS:000371453700025 |
内容类型 | 期刊论文 |
源URL | [http://ir.kib.ac.cn/handle/151853/26005] ![]() |
专题 | 昆明植物研究所_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. |
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