Synthesis of glyco-fused bicyclic compounds; Conformationally constrained scaffolds and useful polyfunctional building blocks

We synthesized fused bicyclic polyfunctional compounds containing a highly hydroxylated pyran ring starting from commercially available methyl glucopyranoside and adopting a RCM annulation approach. The versatile α,β-unsaturated ketone group was introduced on the newly formed ring and, as an example of the potential of these polyfunctionalized building blocks, a tetracyclic compound was synthesized through a Diels-Alder cycloaddition reaction. Bicyclic polyfunctional glycol-fused compounds have been synthesized from commercially available methyl gluco-pyranoside. These molecules, with their high chirality content, presence of an α,β-unsaturated ketone and multiple hydroxyl groups represent useful building blocks for the preparation of complex, optically pure compounds.