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Giulia Bergonzini and Prof. Dr. Paolo Melchiorre Dioxindole in Asymmetric Catalytic Synthesis: Routes to Enantioenriched 3-Substituted 3-Hydroxyoxindoles and the Preparation of Maremycin A Angewandte Chemie International Edition 51

Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201107443

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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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