ALCLASS · Application of Lithiated Carbamates to the Asymmetric Synthesis of Sulfolipid-I

Mycobacterium tuberculosis, the causative agent of human tuberculosis, is unique among bacterial pathogens. Sulfolipid-I (SL-I) is the major constituent metabolite of thick cell wall present in Mycobacterium Tuberculosis (M-TB). SL-I comprises of a disaccharide and four chiral hydrophobic lipid substituents, the overall structure of which is responsible for the resistance of M. Tuberculosis to antibiotics. While SL-I has been shown to elicit specific responses from immune cells, the mechanistic basis of these effects, biosynthesis and biological activities are unknown. Although a number of studies have been reported on the synthesis of disaccharide core and hydrophobic lipids of SL-I, major challenges reside in the synthesis of chiral hydrophobic lipids, which comprise multiple stereocenters. It is aimed to synthesis the enantiopure sulfolipid-I in a short synthesis by utilizing the recent methodology developed by the Aggarwal group involving the reactions of chiral lithiated carbamates with boronic esters. This new strategy is a potentially powerful tool for the iterative asymmetric synthesis of complex molecules in short order.""