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

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 pre...

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Veröffentlicht in:Angewandte Chemie International Edition 2012-01, Vol.51 (4), p.971-974
Hauptverfasser: Bergonzini, Giulia, Melchiorre, Paolo
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201107443