We demonstrate the use of tricarbonyl(tropone)iron (TIC) as a versatile, yet simple starting material for accessing bridged azapolycycles with a seven-membered carbocycle––a structural motif found within a number of pharmaceuticals and biologically active alkaloids. This work includes novel approaches to accessing fused and bridged azabicyclic structures from a cationic derivative of TIC via C–N and C–C bond formations. Following addition of a properly functionalized amine to TIC, different cyclizations leading to diverse polycyclic skeletons becomes possible. Here, we report on these cyclizations, which can proceed by different combinations of demetallation processes and Pd-catalyzed reactions. Further efforts towards cyclizations utilizing organolithium species are also presented. The structural diversity obtainable from simple starting materials and variation of reaction conditions paves the way for rapid syntheses of complex alkaloid-like scaffolds.

Tricarbonyl(tropone)iron as a versatile platform for the synthesis of diverse azapolycycles via intramolecular Heck and related cyclizations

ACS Spring 2022

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