Synthesis of Glycoisoxazoles: A Novel Methodology for Functionalizing the C-1 Position of D-Glucans to Obtain Bioactive Chemical Compounds

Glycals and isoxazoles are important structural motifs due to their wide range of biological activities, including anti-inflammatory, antimicrobial, and anticancer properties. In this work, glycals were explored as versatile building blocks for the synthesis of isoxazole derivatives from ynone precursors. Depending on the reaction conditions, cycloaddition proceeds through 1,2- or 1,4-addition pathways, leading to regioisomeric glycoisoxazoles. This study provides insights into glycal reactivity and regioselective ynone cyclization processes, expanding the scope of carbohydrate-derived heterocycles with potential applications in medicinal chemistry