Oxyfunctionalization of Calixarene Quinone Rings

The epoxidation of quinone rings of calixquinones represents a valid route for the introduction of oxygenated functionalities into the de-tert-butylated calixarene walls originating cis-diepoxy-p-dione moieties. Carbonyl reduction of these systems leads to hybrid calixarenes containing dianhydroinositol moieties (calixinositols) belonging to the calixcyclitols family. The regio- and stereochemistry of these derivatives was determined by 2D NMR studies, in conjunction with MM3 calculations and X-ray crystallography.