Synthesis of Pyrrolo-isoquinolines Related to the Lamellarins Using Silver-Catalyzed Cycloisomerization/Dipolar Cycloaddition

Synthesis of pyrrolo-isoquinolines related to the lamellarin alkaloids employing silver-catalyzed cycloisomerization−dipolar cycloaddition of alkynyl N-benzylidene glycinates is described. Mechanistic studies revealed Ag(I)-catalyzed cycloisomerization to an azomethine ylide as a key step for formation of angular pyrrolo-isoquinolines.

本文报道了利用炔基N-亚苄基甘氨酸酯的银催化环异构化-偶极环加成反应，合成与层孔素生物碱（lamellarin alkaloids）相关的吡咯并异喹啉类化合物的方法。机理研究表明，银(I)催化的环异构化生成甲亚胺叶立德，是构建角型吡咯并异喹啉骨架的关键步骤。