Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2018

Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars

Résumé

We report herein the development of a stereodivergent route towards polyhydroxylated bicyclic azetidine scaffolds, namely 6-azabicyclo[3.2.0]heptane derivatives. The strategy hinges on a common bicyclic β-lactam precursor, which is forged by way of a rare example of a cationic Dieckmann-type reaction, followed by IBX-mediated desaturation. Substrate-controlled diastereoselective oxidations then allow the divergent preparation of novel iminosugar mimics.

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Chimie organique
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Dates et versions

hal-02178491 , version 1 (09-07-2019)

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M Malinowski, Raphael Hensienne, Nicolas Kern, Damien Tardieu, Anne Bodlenner, et al.. Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars. Organic & Biomolecular Chemistry, 2018, 16, pp.4688-4700. ⟨10.1039/C8OB01065J⟩. ⟨hal-02178491⟩
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