Diversity-Oriented Synthesis of Carbohydrate Scaffolds through the Prins Cyclization of Differently Protected D-Mannitol-Derived Homoallylic Alcohols

A diversity-oriented synthesis of a variety of carbohydrate scaffolds, including sugar-fused isochroman derivatives, bicyclic vinyl halide derivatives, fluorine-substituted tetrahydropyrans, and a furan derivative, is reported. This was achieved through the Prins reaction of d-mannitol-derived homoallylic alcohols in which the allylic alcohol bears a different protecting group, leading to structural variation in the products. Some of the products were also converted into more functionalized scaffolds of wider utility and of possible biological importance. Appropriate mechanisms have been proposed to account for the product formation.