石杉碱甲及其类似物吡啶稠合手性双环[3.3.1]壬烷骨架的不对称构建
收稿日期: 2021-05-31
修回日期: 2021-07-07
网络出版日期: 2021-07-20
基金资助
国家自然科学基金(21871152); 国家自然科学基金(92056105); 国家自然科学基金(21532003); 国家自然科学基金(21790332)
Enantioselective Construction of the Pyridine-Fused Chiral Bicyclo- [3.3.1]nonane Skeleton of Huperzine A and Its Analogues
Received date: 2021-05-31
Revised date: 2021-07-07
Online published: 2021-07-20
Supported by
National Natural Science Foundation of China(21871152); National Natural Science Foundation of China(92056105); National Natural Science Foundation of China(21532003); National Natural Science Foundation of China(21790332)
报道了一种不对称构建石杉碱甲及其类似物吡啶稠合手性双环[3.3.1]壬烷骨架的策略. 该策略主要通过具有环外双键的γ,δ-不饱和β-酮酸酯的动态动力学拆分不对称催化氢化, 并结合分子内芳基化反应为关键步骤来不对称构建吡啶稠合手性双环[3.3.1]壬烷骨架. 依据此策略, 从已知的原料出发, 经5步反应以17.4%的总收率完成了石杉碱甲及其类似物核心手性骨架结构的简洁、快速不对称构建.
关键词： 芳基化反应; 不对称催化氢化; 双环[3.3.1]壬烷骨架; 石杉碱甲; 不饱和酮酸酯
宾怀玉 , 程立 , 杨小会 , 谢建华 , 周其林 . 石杉碱甲及其类似物吡啶稠合手性双环[3.3.1]壬烷骨架的不对称构建[J]. 有机化学, 2021 , 41(10) : 4021 -4027 . DOI: 10.6023/cjoc202105059
A concise strategy for the enantioselective construction of the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton of (+)-huperzine A and its nanlogues was reported. The key features of this strategy are the catalytic asymmetric hydrogenation of an exocyclic γ,δ-unsaturated β-ketoester via dynamic kinetic resolution combined with an intramolecular arylation as the key steps to constuct the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton. This strategy provides a concise and rapid approach to the chiral core structure of huperzine A and its nanlogues from the known starting materials (5 steps and 17.4% overall yield).
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