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A new approach to the bicyclo[3.3.1]nonane framework of huperzine A-like molecules via palladium-catalyzed intramolecular γ-arylation 被引量:2

A new approach to the bicyclo[3.3.1]nonane framework of huperzine A-like molecules via palladium-catalyzed intramolecular γ-arylation
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摘要 In our synthetic studies toward huperzine A, a diastereoselective α'-alkylation of the α-amido-γ-methyl hexenone 4 was real- ized through a dianion intermediate which significantly enhanced the reactivity. Under the attempted Heck reaction conditions, an unexpected and unprecedented palladium-catalyzed intramolecular T-arylation of 3 was observed, which generated 18 with bicyclo[3.3, l]nonane framework in satisfactory yield. In our synthetic studies toward huperzine A, a diastereoselective α′-alkylation of the α-amido-γ-methyl hexenone 4 was realized through a dianion intermediate which significantly enhanced the reactivity. Under the attempted Heck reaction conditions, an unexpected and unprecedented palladium-catalyzed intramolecular γ-arylation of 3 was observed, which generated 18 with bicyclo[3.3.1]nonane framework in satisfactory yield.
出处 《Science China Chemistry》 SCIE EI CAS 2012年第6期1097-1100,共4页 中国科学(化学英文版)
基金 supported by the National Natural Science Foundation of China (20902101 & 21172246) National Basic Research Program of China (973 Program) (2010CB833206)
关键词 huperzine A bicyclo[3.3.1]nonane γ-arylation 芳基化反应 石杉碱甲 钯催化 分子 框架 双环 高反应性 反应条件
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