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Glycals (carbohydrate enol-ethers) have enjoyed profound applications in organic synthesis for
more than a century. They not only serve as versatile glycosyl donors or as substrates for Ferrier
rearrangement but also find extensive synthetic applications especially as a “chiral pool” for
accomplishing the synthesis of a variety of natural and biologically important compounds. As
cyclic enol ethers, they demonstrate high reactivity and are among the most sought-after
monosaccharide derivatives. Over the years, we have utilized glycals as a class of versatile
synthons and accomplished the total synthesis variety of biologically important nitrogen
heterocycles and carbocycles through a “Diversity Oriented Approach”. Our synthetic strategy in
this direction mainly relied on the cleavage of ring O-C bond of the sugar. Very recently, we have
embarked on the chemistry of 2-aminoglycosyl azides and have developed novel route to the
synthesis of hypoglycemic agents, potential hepatitis B virus (HBV) inhibitors. Some of these
research outcomes will be presented. |