Total Synthesis of Sinensilactam A
Total Synthesis of Sinensilactam A
复制标题
硅内酰胺A的全合成
DOI：
10.1021/acs.orglett.8b00380
复制
发表时间：
2018
期刊：
影响因子：
5.2
通讯作者：
Yang Zhen
中科院分区：
文献类型：
--
作者：
Shao Wenbin;Huang Jun;Guo Kai;Gong Jianxian;Yang Zhen
天然存在的 (±)-sinensilactam A 的全合成通过 18 个步骤实现。这项工作的关键步骤是铑催化的[3 + 2]环加成反应，用于构建两个全碳邻位四元中心，以及原位生成的N-酰亚胺中间体与醛20的会聚串联缩合。这使得在后期能够实施统一的策略来立体选择性地形成sinensilactam A的四环半缩醛核。使用该策略也实现了applanatumol F和C8-epi-applanatumol D的全合成。
The total synthesis of naturally occurring (±)-sinensilactam A was achieved in 18 steps. The key steps of this work are a rhodium-catalyzed [3 + 2] cycloaddition for construction of the two all-carbon vicinal quaternary centers and a convergent and tandem condensation of the in situ generatedN-acyliminium intermediate with aldehyde20. This enabled implementation of a unified strategy for stereoselective formation of the tetracyclic hemiaminal core of sinensilactam A in a later stage. The total syntheses of applanatumol F and C8-epi-applanatumol D are also achieved using this strategy.