Iridium-Catalyzed Enantioselective Indole Cyclization: Application to the Total Synthesis and Absolute Stereochemical Assignment of (-)-AspidophyllineA
Jiang, Shi-Zhi1; Zeng, Xue-Yi1,2; Liang, Xiao1,2; Lei, Ting1; Wei, Kun1; Yang, Yu-Rong1
2016-03-14
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume55Issue:12Pages:4044-4048
AbstractThe first enantioselective total synthesis of (-)-aspidophyllineA, including assignment of its absolute configuration has been accomplished. A key element of the synthesis is a highly enantioselective indole allylic alkylation/iminium cyclization cascade which was developed by employing a combination of Lewis acid activation and an iridium/ligand catalyst. This strategy relies on the direct use of 2,3-disubstituted indoles with secondary allylic alcohols appended at C2 and heteronucleophiles appended at C3, indoles which are easily prepared from simple starting materials under C-H activation conditions.
KeywordCyclizations Enantioselectivity Indoles Iridium Total Synthesis
DOI10.1002/anie.201511549
Indexed BySCI ; IC ; CCR
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000372660400033
Citation statistics
Cited Times:66[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/26181
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, Lanhei 132, Kunming 650201, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100039, Peoples R China
Recommended Citation
GB/T 7714
Jiang, Shi-Zhi,Zeng, Xue-Yi,Liang, Xiao,et al. Iridium-Catalyzed Enantioselective Indole Cyclization: Application to the Total Synthesis and Absolute Stereochemical Assignment of (-)-AspidophyllineA[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2016,55(12):4044-4048.
APA Jiang, Shi-Zhi,Zeng, Xue-Yi,Liang, Xiao,Lei, Ting,Wei, Kun,&Yang, Yu-Rong.(2016).Iridium-Catalyzed Enantioselective Indole Cyclization: Application to the Total Synthesis and Absolute Stereochemical Assignment of (-)-AspidophyllineA.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,55(12),4044-4048.
MLA Jiang, Shi-Zhi,et al."Iridium-Catalyzed Enantioselective Indole Cyclization: Application to the Total Synthesis and Absolute Stereochemical Assignment of (-)-AspidophyllineA".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55.12(2016):4044-4048.
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