Hydroxyoxindole derivatives are a key structural element of many natural products. Therefore, their stereoselective synthesis have become a challenge for many organic chemists.

In this paper, Paolo Melchiorre and Giulia Bergonzini describe an unprecedented synthetic strategy to access 3-substituted-3-hydroxyoxindole derivatives in excellent yields and enantioselectivities.
Their synthetic pathway focuses on the understanding of dioxindole’s nucleophilicity to develop a productive synthetic route.

They use this methodology for the straightforward synthesis of Maremycin A, a marine natural product, and they believe that this previously unexplored reactivity will rapidly find applications in the design of other catalytic asymmetric transformations.