Efficient Synthesis of Direct Precursors of the Carbohydrate Moiety of New Antibacterials 6-Epi-VIC-105555 and 6-Epi-VIC-II

Abstract

In search for new antibiotics we have developed a novel route leading to direct precursors of the carbohydrate moieties of new promising antibacterial agents 6-epi-VIC-105555 and 6-epi-VIC-II. The presented synthetic strategy consists of using as starting material the readily available β-dibenzylamino-α-ketoester and application of a sequence of chemical transformations on C-7: olefination or methylation, reduction, deoxygenation of the terminal alcohol, and finally hydrogenation. The desired molecules were obtained in a stereoselective fashion and with good overall yields.