DEVELOPMENT OF METHODOLOGY BASED ON THE USE OF THE 7-OXABICYCLO[2.2.1]HEPTANYL SYSTEM FOR THE PREPARATION OF CARBOHYDRATE-DERIVATIVES

The 7-oxabicyclo[2.2.1]heptanyl system provides a rapid entry to carbo hydrate derivatives in a stereoselective manner by virtue of the rigid framework. The formation of this bicyclic system through a Diels-Alde r reaction of furan with a number of dienophiles is influenced by the substitution on the dienophile. Use of an anion stabilising group as a carbonyl equivalent has previously led to a ring opening reaction of the bicyclic system. However, anion chemistry can be used to functiona lise the bicyclic system, and used for the introduction of a hydroxy g roup that allows, in turn, a method for the preparation of hexose deri vatives.