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 ,-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.