Manipulations of phenylnorbornyl palladium species for multicomponent construction of a bridged polycyclic privileged scaffold.
Manipulations of phenylnorbornyl palladium species for multicomponent construction of a bridged polycyclic privileged scaffold.
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操纵苯基降冰片基钯物质用于桥联多环优先支架的多组分构建
DOI：
10.1038/s42004-022-00759-4
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发表时间：
2022-10-29
影响因子：
5.9
通讯作者：
Hu, Qingzhong
中科院分区：
文献类型：
--
作者：
Yin, Lina;Guan, Ting;Cheng, Jie;Pan, Dongchao;Lu, Jinyang;Huang, Jiahui;Wu, Jiaqi;Chen, Xiaoli;You, Taiyun;Huo, Xuting;He, Yuting;Pang, Jiayun;Hu, Qingzhong
六氢甲咔唑由于其结构复杂性和受体结合时最小化的熵罚之间的良好平衡，在新药和光敏有机材料的发现中是一种特权支架。为了解决合成这种高度期望的桥连多环支架的困难，我们设计了一个方便的多组分反应级联，如截取的Heck加成/C-H活化/C-钯配体形成/ANP的亲电攻击/N-钯配体形成/Buchwald胺化。这种复杂策略的一个显著特征是连续生成两种关键的苯基基钯物质，以控制朝向所需产物的反应流。DFT计算进一步揭示了Cs2 CO 3和5，6-二酯取代在防止多个副反应中的关键作用。这种创新的方法表现出广泛的范围与良好的产率，因此，将使天然产物的基础上六氢甲咔唑类化合物库的建设。
Hexahydromethanocarbazole is a privileged scaffold in the discovery of new drugs and photoactive organic materials due to its good balance between structural complexity and minimized entropy penalty upon receptor binding. To address the difficulty of synthesizing this highly desirable bridged polycyclic scaffold, we designed a convenient multicomponent reaction cascade as intercepted Heck addition/C-H activation/C-palladacycle formation/electrophilic attack of ANP/N-palladacycle formation/Buchwald amination. A distinguishing feature of this sophisticated strategy is the successive generation of two key phenylnorbornyl palladium species to control the reaction flow towards desired products. DFT calculations further reveal the crucial roles of Cs2CO3and 5,6-diester substitutions on the norbornene reactant in preventing multiple side-reactions. This innovative method exhibits a broad scope with good yields, and therefore will enable the construction of natural-product-like compound libraries based on hexahydromethanocarbazole.
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