Défense de thèse de doctorat en sciences chimiques

The first project of this thesis is dedicated to the study and the development of new debenzylative cyclization reactions to construct five-membered ring glycomimetics with various applications in bio-organic chemistry. Although benzyl ether constitutes a major class of protecting groups, debenzylative cyclization may occurs when a 1,4-relationship exist between an electrophilic center and a benzyl ether, to yield a tetrahydrofuran unit. The cyclization is highly stereo- and regio-selective in favor of five-membered ring over the tetrahydropyran isomer, thus suppressing the need of protecting group manipulation to ensure regioselective cyclization.
The second project deals with the multi-step synthesis of difluorinated substrate analogues of UDP-Galactopyranose Mutase (UGM). This enzyme is involved in the biosynthesis of the bacteria cell-wall of mycobacterium tuberculosis, the causative agent of tuberculosis (TB). Despite the availability of treatments, TB still remains a major threat for public health, mainly due to the emergence of multidrug resistant strains.