The first synthesis of cyclic benzopyridoiodolium salts is described.
These hypervalent iodine intermediates are used in an efficient
strategy for the construction of the δ-carboline core.
This novel approach involves a twofold palladium-catalyzed Buchwald-Hartwig
reaction between these unprecedented reagents and a primary amine.
Our methodology successfully provides the expected N-substituted δ-carboline
core and is efficiently applied in the total synthesis of quindoline.
alkaloids - amination - heterocycles - iodine - total synthesis
