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Catalytic Asymmetric Total Synthesis of (-)-Galanthamine and (-)-Lycoramine
Li, Lei; Yang, Qiao; Wang, Yuan; Jia, Yanxing
关键词alkaloids asymmetric catalysis natural products palladium total synthesis
刊名ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
2015-05-18
DOI10.1002/anie.201411338
54期:21页:6255-6259
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Multidisciplinary
资助者National Natural Science Foundation of China ; National Natural Science Foundation of China
研究领域[WOS]Chemistry
关键词[WOS]MICHAEL ADDITION-REACTIONS ; LAROCK INDOLE SYNTHESIS ; ENANTIOSELECTIVE SYNTHESIS ; 3-SUBSTITUTED BENZOFURAN-2(3H)-ONES ; AMARYLLIDACEAE ALKALOIDS ; BIOMIMETIC SYNTHESIS ; TRICYCLIC INDOLES ; INTERNAL ALKYNES ; FORMAL SYNTHESIS ; (+/-)-GALANTHAMINE
英文摘要

The catalytic asymmetric total syntheses of (-)-galanthamine (1) and (-)-lycoramine (2) have been achieved by using a conceptually new strategy featuring two metal-catalyzed reactions as the key steps. A new method for the construction of 3,4-fused benzofurans has been developed through a palladium-catalyzed intramolecular Larock annulation reaction, which was successfully applied to the construction of the ABD tricyclic skeleton of 1 and 2. To achieve the asymmetric synthesis of 1 and 2, a Sc-III/N,N-dioxide complex was used to catalyze the enantioselective conjugate addition of 3-alkyl-substituted benzofuranone to methyl vinyl ketone for the construction of a chiral quaternary carbon center.

语种英语
所属项目编号21402003 ; 21290183
资助者National Natural Science Foundation of China ; National Natural Science Foundation of China
WOS记录号WOS:000354260000025
引用统计
被引频次:25[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/61669
专题北京大学药学院
作者单位Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Li, Lei,Yang, Qiao,Wang, Yuan,et al. Catalytic Asymmetric Total Synthesis of (-)-Galanthamine and (-)-Lycoramine[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2015,54(21):6255-6259.
APA Li, Lei,Yang, Qiao,Wang, Yuan,&Jia, Yanxing.(2015).Catalytic Asymmetric Total Synthesis of (-)-Galanthamine and (-)-Lycoramine.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,54(21),6255-6259.
MLA Li, Lei,et al."Catalytic Asymmetric Total Synthesis of (-)-Galanthamine and (-)-Lycoramine".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 54.21(2015):6255-6259.
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