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Dioxindole in Asymmetric Catalytic Synthesis: Routes to Enantioenriched 3‐Substituted 3‐Hydroxyoxindoles and the Preparation of Maremycin A
Author(s) -
Bergonzini Giulia,
Melchiorre Paolo
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201107443
Subject(s) - reactivity (psychology) , oxindole , computer science , product (mathematics) , nucleophile , key (lock) , combinatorial chemistry , chemistry , catalysis , organic chemistry , mathematics , medicine , alternative medicine , geometry , pathology , computer security
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.