Organocatalytic Synthesis and Anti‐Trypanosomal Activity Evaluation of L‐Pentofuranose‐Mimetic Iminosugars

Abstract

A series of L‐lyxo and L‐xylo‐ pentofuranose‐mimetic iminosugars and derivatives were efficiently synthesized in a stereoselective manner, through a concise strategy which involves an organocatalyzed Mannich reaction of an imine and a protected dioxanone as key step, using D‐proline as catalyst. A preliminary evaluation of their activity as potential anti‐trypanosomal agents was studied. One of the synthesized compounds showed an interesting activity against bloodstream Trypanosoma brucei brucei (EC50=3.8±1.0 μM).