10.1021/jo010579z.s002 Kevin R. Roesch Kevin R. Roesch Richard C. Larock Richard C. Larock Synthesis of Isoquinolines and Pyridines by the Palladium/Copper-Catalyzed Coupling and Cyclization of Terminal Acetylenes and Unsaturated Imines:  The Total Synthesis of Decumbenine B American Chemical Society 2001 product decumbenine B aryl cyclization conditions isoquinoline heterocycles Terminal Acetylenes alkenyl acetylenes cyclize terminal acetylenes terminal acetylene iminoalkyne Total Synthesis yield palladium catalyst Decumbenine B Monosubstituted isoquinolines cyclization methodology 2001-12-12 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Isoquinolines_and_Pyridines_by_the_Palladium_Copper-Catalyzed_Coupling_and_Cyclization_of_Terminal_Acetylenes_and_Unsaturated_Imines_The_Total_Synthesis_of_Decumbenine_B/3689907 Monosubstituted isoquinolines and pyridines have been prepared in good to excellent yields via coupling of terminal acetylenes with the <i>tert</i>-butylimines of <i>o</i>-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst and subsequent copper-catalyzed cyclization of the intermediate iminoalkynes. In addition, isoquinoline heterocycles have been prepared in excellent yields via copper-catalyzed cyclization of iminoalkynes. The choice of cyclization conditions is dependent upon the nature of the terminal acetylene that is employed, as only aryl and alkenyl acetylenes cyclize under the palladium-catalyzed reaction conditions that have been developed. However, aryl-, vinylic-, and alkyl-substituted acetylenes undergo palladium-catalyzed coupling and subsequent copper-catalyzed cyclization in excellent yields. The total synthesis of the isoquinoline natural product decumbenine B has been accomplished in seven steps and 20% overall yield by employing this palladium-catalyzed coupling and cyclization methodology.