海洋生物碱Aaptamine的全合成

Total synthesis of Aaptamine

目的设计了一条高效的海洋生物碱Aaptamine的合成路线。方法该合成路线使用廉价易得的6,7-二甲氧基四氢异喹啉为原料,经过六步反应成功合成目标天然产物,总产率约为21%。全合成中的关键步骤包括甲基化反应和在布朗斯特酸的作用下,Vilsmeier试剂促进关环生成苯并[de][1,6]萘啶骨架结构。结论关键中间体和产物结构经~1H-NMR、~(13)C-NMR和HR-MS(ESI)进行了确证。本文所提供的合成路线简单易行、合成步骤相对较短,为Aaptamine类生物碱的开发应用奠定了基础。

Objective To develop an efficient synthetic route of Aaptamine,a marine alkaloid in this study.Methods Starting from readily available 6,7⁃dimethoxytetrahydroisoquinoline,the target natural product can be synthesized successfully in six steps with an overall yield of approximately 21%.The key steps in the synthesis involved a methylation and a cyclization promoted by Vilsmeier reagent in the presence of Brønsted acid,leading to the formation of a benzo[de][1,6]naphthyridine skeleton.Conclusion The structures of all intermediates and target product are confirmed by 1H⁃NMR,13C⁃NMR and HR⁃MS(ESI).The synthetic route is straightforward and efficient,with relatively short steps,laying a foundation for the development and application of Aaptamine⁃type alkaloids.