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Nouvelles classes d’iminosucres bicycliques : approche synthétique des squelettes 5-azaspiro[3.4]octane et 6-azabicyclo[3.2.0]heptane

Abstract : Previous studies performed by our group led to the identification of α-1-C-nonyl-1,5-dideoxy-1,5-imino-D-xylitol as a powerful inhibitor of β-glucocerebrosidase, the enzyme involved in Gaucher disease. This compound’s unusual (inverted chair) conformation prompted us to further study the relationship between iminosugars’ conformation and biological activity. The aim of this PhD work was thus the synthesis of conformationally restricted iminosugar analogues. Firstly, three spiro-iminosugars based on a 5-azaspiro[3.4]octane scaffold were synthesized through a sequence including three key steps: cyclobutane formation by way of radical cyclisation, nitrogen introduction by mean of C-H amination and pyrrolidine formation by way ofmetathesis. Secondly, we developed a sequence dedicated to the stereodivergent synthesis of fused bicyclic iminosugars based on a 6-azabicyclo[3.2.0]heptane scaffold through a succession of two key steps: azabicyclic scaffold formation by mean of Mukaiyama aldol reaction followed by ketone to enone oxidation.
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Raphaël Hensienne. Nouvelles classes d’iminosucres bicycliques : approche synthétique des squelettes 5-azaspiro[3.4]octane et 6-azabicyclo[3.2.0]heptane. Autre. Université de Strasbourg, 2016. Français. ⟨NNT : 2016STRAF049⟩. ⟨tel-01674249v2⟩

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