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5,5,8aβ-三甲基-6β-羟基-反八氢-1-萘酮的合成及在Phenylspirodrimane类混源萜天然产物骨架构建中的应用
Synthesis of 6β-Hydroxy-5,5,8aβ-trimethyloctahydronaphthalen-1(2H)-one Toward the Establishment of the Scaffold of Phenylspirodrimane Meroterpenoid Natural Products
【摘要】 以(E)-5,9-二甲基-4,8-癸二烯酸乙酯为原料,发展了一种合成5,5,8aβ-三甲基-6β-羟基-反八氢-1-萘酮(1)的新方法,并将其成功应用于phenylspirodrimane类混源萜天然产物骨架的构建.对合成过程中所涉及的关键反应如区域选择性环氧化和Cp2TiCl催化的自由基串联环合反应进行了优化.所合成化合物的结构均通过核磁共振波谱(NMR)和高分辨质谱(HRMS)进行了表征和确认.
【Abstract】 Starting from ethyl(E)-5,9-dimethyldeca-4,8-dienoate,we developed a method for the synthesis of 6β-hydroxy-5,5,8aβ-trimethyloctahydronaphthalen-1-one(1),which was successfully applied to the establishment of the skeleton of phenylspirodrimane meroterpenoid natural products. Key steps such as regioselective epoxidation and Cp2TiCl-promoted radical cascade cyclization have been optimized. The structures of the compounds synthesized have been characterized with nuclear magnetic resonance spectroscopy( NMR) and high resolution mass spectrometry( HRMS).
【Key words】 6β-Hydroxy-5,5,8aβ-trimethyloctahydronaphthalen-1(2H)-one; Phenylspirodrimanes meroterpenoids; Epoxidation; Free radical tandem cyclization;
- 【文献出处】 高等学校化学学报 ,Chemical Journal of Chinese Universities , 编辑部邮箱 ,2020年05期
- 【分类号】TQ28
- 【下载频次】74