Figure 1.

Proposed design strategy to derive novel indole alkaloids from the Cinchona alkaloids. a) The Cinchona alkaloids and representative 2,3‐fused indole alkaloids. b) The targeted unnatural indole alkaloids derived from Cinchona alkaloids. c) Proposed synthetic route to the pseudo‐NPs by harnessing a Pd‐catalyzed annulation between the quinidine/quinine‐derived ketones 5 and 6 and 2‐iodoanilines. *Stereochemistry relative to compounds 1 and 2 as appropriate.