An attempted oxidative coupling approach to the scholarinine A framework

Abstract

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.