LAUSR

A diversity oriented synthesis of a variety of carbohydrate scaffolds such as sugar fused isochroman derivatives, bicyclic vinyl halide derivatives, fluorine substituted tetrahydropyrans, and a furan derivative is reported. This has been achieved by using the Prins reaction on D-mannitol derived homoallylic alcohols in which the allylic alcohol is differently protected and that causes structural variations in products. Some of the products have also been converted into more functionalized scaffolds of wider utility and of possible biological importance. Appropriate mechanisms have been proposed to account for the product formation.