Dioxindole in Asymmetric Catalytic Synthesis: Routes to Enantioenriched 3-Substituted 3-Hydroxyoxindoles and the Preparation of Maremycin A

Authors


  • Support from the Institute of Chemical Research of Catalonia (ICIQ) Foundation and from MICINN (grant CTQ2010-15513) is gratefully acknowledged. G.B. is grateful to the MEC for an FPU predoctoral fellowship.

Abstract

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Taming the reactivity: Understanding the nucleophilicity of dioxindole under different reaction conditions is key to a direct and easy access to valuable spiro oxindole γ butyrolactones and 3-substituted 3-hydroxyoxindole derivatives in excellent yields and enantioselectivities (see scheme). The preparation of maremycin A serves as an example for the potential usefulness of this previously unexplored reactivity in natural product synthesis.

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