Synthesis of Stereodivergent Chirally Pure Acyclic Polyols Based Quinone-Triazole Glycohybrids as Privileged Scaffolds.

Quinones are privileged redox-active scaffolds in medicinal chemistry, yet their clinical utility is often limited by poor solubility and nonspecific toxicity. To address this, we developed a stereodivergent, one-pot strategy for the synthesis of quinone-triazole [3 + 2] adducts as structurally defined polyol-based glycohybrids. The tandem process involves nucleophilic addition of 5-azido-2,3-dideoxy glycols to electrophilic 1,4-quinones, followed by intramolecular cycloaddition and proton transfer to furnish the fused products with an acyclic polyol chain. The protocol delivers a broad range of quinone-triazole glycohybrids in good to excellent yields, with high functional group tolerance on both the quinone and glycol components, providing an efficient route to quinone-triazole redox-active small glycohybrids as privileged scaffolds.