An attempted oxidative coupling approach to the scholarinine A framework.

In this manuscript, an oxidative carbon-carbon bond forming reaction to construct the framework of alkaloids such as scholarinine A is explored using a constrained substrate. Instead of the desired carbon-carbon bond formation between an indole C3 position and a malonate group, a competing carbon-nitrogen bond between the malonate and indole C3 position was observed to form. This work adds to the growing body of substrates for oxidative carbon-carbon bond formation and importantly, demonstrates that these reactions are challenging for some conformationally constrained substrates.