Carbohydrate-spiro-heterocycles

1. Front Matter

   Pages i-vii

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

   • Maxime Pommier, Sébastien Vidal

   Pages 1-25

3. Cycloaddition Reactions of Sugar-Based Olefins, Nitrones and Nitrile Oxides: En Route to Saccharidic Spiroisoxazoli(di)nes

   • Nadia Pellegrini-Moïse, Mylène Richard

   Pages 27-49

4. Carbohydrate Spiro-heterocycles via Radical Chemistry

   • Angeles Martín, Ernesto Suárez

   Pages 51-104

5. Carbohydrate-Derived Spiroketals and Spirocyclic Lactones

   • Perali Ramu Sridhar

   Pages 105-136

6. Cyanohydrins and Aminocyanides as Key Intermediates to Various Spiroheterocyclic Sugars

   • Solen Josse, Denis Postel

   Pages 137-169

7. Recent Advances in the Chemistry and Biology of Spirocyclic Nucleosides

   • Martín Soto, Humberto Rodríguez-Solla, Raquel Soengas

   Pages 171-213

8. Spiroketal Phthalane C-Glycosides: Synthesis of Papulacandins and SGLT2 Inhibitors

   • Yoshihiko Yamamoto

   Pages 215-260

9. Spiro Iminosugars: Structural Diversity and Synthetic Strategies

   • Damien Hazelard, Raphaël Hensienne, Jean-Bernard Behr, Philippe Compain

   Pages 261-290

10. Back Matter

    Pages 291-295

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This volume is devoted to compounds in which the spiro centre is part of a pyranoid or furanoid or an iminosugar ring. The chapters contributed deal with methodological peculiarities of syntheses of natural and artificial sugar derived spirocycles as well as their biological applications and other utilities including marketed drugs. Carbohydrates are ubiquitous molecules in nature and participate in a vast number of biological interactions. Especially their conjugates with practically all kinds of primary and secondary metabolic small molecules (and also biomacromolecules) representing valuable tools for glycobiology research and also lead compounds for drug discovery. While monosaccharides per se appear as heterocycles, their natural conjugates frequently exhibit spiro(hetero)cyclic derivatives, in many cases of high therapeutical relevance. As a consequence, the field of carbohydrate-spiro-heterocycles attracts intense interest from both chemical and biomedical aspects therefore this volume will be of interest for synthetic and medicinal chemists and (glyco)biologists, as well as researchers involved in various biomedical fields.

• Spiro-annulated carbohydrate
• Cycloaddition reactions
• radical chemistry
• spirocyclic lactones
• spirocyclic nucleosides
• Cyanhydrine and aminocyanide
• spirocyclization for carbohydrates

• Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary

  László Somsák

László Somsák is a full Professor and Head of the Department of Organic Chemistry at the University of Debrecen, Hungary. He serves as an editorial board member for Carbohydrate Research, and as guest editor for special issues of Carbohydrate Research, Mini-Reviews in Medicinal Chemistry, Molecules. His research interests include synthetic carbohydrate chemistry directed to C-glycosyl compounds, anomeric-spirocycles, glycals, exo-glycals and their derivatives; development of synthetic methodology involving radicals and carbenes; synthesis of glycosidase and glycogen phosphorylase inhibitors as potential antidiabetics, study of their structure-activity relationships; synthesis of glycomimetics and glycopeptidomimetics.

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