Conduritols: Synthesis strategies from classic to contemporary

Abstract

Conduritols, cyclic polyols with diverse biological activities, have garnered significant attention since their discovery over a century ago. These compounds, comprising six isomers (A, B, C, D, E, and F), possess unique structural and stereochemical properties, with only A and F naturally occurring. Conduritols and their derivatives serve as essential precursors for biologically significant molecules, including cyclitols, pseudo-sugars, and phosphorylated inositols. Their applications span a wide range of biological processes, such as glycosidase inhibition, insulin modulation, and signal transduction, making them promising candidates for therapeutic interventions in diabetes, cancer, and HIV/AIDS.

Synthetic advancements have enabled the preparation of all conduritol isomers, employing innovative approaches like aromatic diol transformations and stereocontrolled reactions. These methods have unlocked efficient pathways to biologically potent compounds, including pancratistatin, narciclasine, and aminoglycosidic antibiotics. This review provides an overview of the historical progress, synthetic methodologies, and biological significance of conduritols. Recent innovations in stereospecific synthesis are highlighted, showcasing the potential for large-scale production of optically pure conduritols to meet growing biomedical demands. This study aims to highlight advancements in conduritol synthesis, focusing on evolving methodologies and stereoselectivity challenges.