Palladium-Catalyzed Synthesis of 1-Vinyltetrahydro-β-carbolines and Aza-spiroindolenines: Access to the Syntheses of 1-Vinyl-β-carbolines and Eudistomins Y1 and Y2.

A general synthesis of 1-vinyltetrahydro-β-carbolines (THBCs) has been achieved via palladium(0)-catalyzed cyclocondensation between allenyltryptamines and aryl iodides. Aza-spiroindolenines could also be accessed from the N-unsubstituted indole substrates by simply tweaking the reaction conditions. DDQ-mediated oxidation of THBCs easily afforded β-carbolines, which could be synthetically transformed into 1-aroyl-β-carbolines of pharmacological interest. Formal total syntheses of eudistomins Y1 and Y2 have also been achieved.