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学科主题: 药学
题名:
Catalytic Asymmetric Total Synthesis of (-)-Galanthamine and (-)-Lycoramine
作者: 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
发表日期: 2015-05-18
DOI: 10.1002/anie.201411338
卷: 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
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
项目资助者: National Natural Science Foundation of China
WOS记录号: WOS:000354260000025
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/61669
Appears in Collections:北京大学药学院_期刊论文

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作者单位: Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

Recommended Citation:
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.
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