An approach towards the construction of the tetracyclic skeleton of palhinine alkaloids
An approach towards the construction of the tetracyclic skeleton of palhinine alkaloids
复制标题
palhinine 生物碱四环骨架的构建方法
DOI：
10.1039/d0qo00554a
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发表时间：
2020-08-21
影响因子：
5.4
通讯作者：
He, Shuzhong
中科院分区：
文献类型：
--
作者：
Han, Congcong;Chen, Yang;He, Shuzhong
本文报道了一种具有四环骨架的palhinine生物碱的简明合成方法。该方法的特征在于双官能刘易斯酸促进的狄尔斯-阿尔德/碳环化级联，用于快速构建异癸烷（三环[4.3.1.0（3，7）]癸烷）核心。该关键反应具有高度的非对映选择性，可以在克级规模上进行。环化产物已经具有完整的palhinine生物碱环系统，并可能进一步官能化为palhinine A。
A concise synthesis of the tetracyclic skeleton of palhinine alkaloids is described. The approach features a bifunctional Lewis acid promoted Diels-Alder/carbocyclization cascade for the rapid construction of the isotwistane (tricyclo[4.3.1.0(3,7)]decane) core. This key reaction is highly diastereoselective and could be carried out on gram scale. The cyclization product already possesses the completed ring system of palhinine alkaloids and could potentially be further functionalized to palhinine A.