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Anomeric Spiro-Annulated Glycopyranosides: An Overview of Synthetic Methodologies and Biological Applications

  • Maxime Pommier
  • Sébastien VidalEmail author
Chapter
  • 179 Downloads
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 57)

Abstract

Organic chemistry developed a series of synthetic strategies toward spiro-annulated carbohydrates as potential pharmaceutical drugs or developed new organic synthetic methodologies. The present chapter gives a general overview of the spiro-annulation of carbohydrates at the anomeric position. The main synthetic strategies can be summarized in five paths. Intramolecular cyclizations can be performed through two short tethers with their reactive ends generating the spirocycle or through a single tether reacting at the anomeric position for cyclization. The three other strategies rely on intermolecular reactions with a portion of the spirocycle only in the external substrate or also on the carbohydrate. Radical-mediated cyclization and cycloaddition reactions are the main strategies toward spiro-annulated carbohydrates. A special attention is paid to discussion of the stereocontrol of the anomeric configuration and also to yields in industrial syntheses or biological activities of the molecules. A specific attention is devoted to tofogliflozin and glycogen phosphorylase inhibitors both used as antihyperglycemic drugs and drug candidates, respectively.

Keywords

1,3-Dipolar cycloaddition Cycloaddition Glycogen phosphorylase Hydrogen atom transfer (HAT) Medicinal chemistry Radical cyclization Ring-closing metathesis SGLT2 Spiroketal Spiro-lactam Type 2 diabetes 

Notes

Acknowledgments

The authors thank the Université Claude Bernard Lyon 1 and the CNRS for financial support. MP is grateful to the Ministère de l’Enseignement supérieur et de la Recherche for a PhD stipend.

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Authors and Affiliations

  1. 1.Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (UMR 5246)Université Claude Bernard Lyon 1 and CNRS, Bâtiment LedererVilleurbanneFrance

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