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Issue 25, 2018
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Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars

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Abstract

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.

Graphical abstract: Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars

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Publication details

The article was received on 07 May 2018, accepted on 05 Jun 2018 and first published on 05 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB01065J
Citation: Org. Biomol. Chem., 2018,16, 4688-4700
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    Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars

    M. Malinowski, R. Hensienne, N. Kern, D. Tardieu, A. Bodlenner, D. Hazelard and P. Compain, Org. Biomol. Chem., 2018, 16, 4688
    DOI: 10.1039/C8OB01065J

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