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

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http://dx.doi.org/10.1021/acs.joc.0c02651DOI Listing

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