Synthesis of polyoxygenated heterocycles by diastereoselective functionalization of a bio-based chiral aldehyde exploiting the Passerini reaction

A chiral bio-based building block, prepared by the lipase-mediated desymmetrization of an erythritol derivative, was further functionalized and then submitted to stereoselective Passerini reactions, allowing the synthesis of a small library of new molecules. Thanks to the presence of different functional groups, further cyclizations were performed providing bicyclic polyoxygenated heterocycles.