Towards Organoboron-mediated Functionalization of Erythromycin A and Synthesis of its Aglycon

Many natural products, including antibiotics, are structurally complex and contain a wide variety of functional groups. As a consequence, the selective functionalization of these molecules often requires the use of inefficient protecting group strategies. Inspired by this obstacle, our group recently developed a borinic acid-catalyzed method to regioselectively functionalize the equatorial position of cis-vicinal diols in carbohydrates with limited use of protecting groups.The work presented in this thesis describes progress made towards selective functionalization of the cis-vicinal diol present in the macrolide antibiotic erythromycin A. This was attempted using the boronic and borinic acid-mediated methodologies developed previously in our group. Finally, a semisynthesis of erythronolide A was carried out with the goal of using our methodology to prepare novel analogues for biological evaluation.M.Sc