One-Pot Conversion of Proline Derivatives into Iodinated Iminosugar-Based Nucleosides, Useful Precursors of Highly Functionalized Nucleoside Analogues

Abstract

Readily available proline derivatives can be transformed in one step into β-iodinated iminosugar-based nucleosides, under very mild conditions. The method couples a tandem radical decarboxylation–oxidation–β-iodination to the addition of nitrogen bases. The iodo group is introduced into the previously unfunctionalized 3-position. The resultant β-iodo derivatives are useful precursors of highly functionalizednucleoside analogues.