The Chemistry of C-Glycosides

Introduction
Organization of the book. Definition and nomenclature of C-Glycosides. O-Glycosides vs C-Glycosides: comparisons of physical properties, anomeric effects, H-bonding abilities, stabilities and conformations. Natural occurring C-Glycosides. C-Glycosides as stable pharmacophores. Further reading. References.

Electrophilic Substitutions
Introduction. Anomeric activating groups and stereoselectivity. Cyanation reactions. Alkylation, allenylation, allylation and alkynation reactions. Arylation reactions. Reactions with enol ethers, silylenol ethers and enamines. Nitroalkylation reactions. Reactions with allylic ethers. Wittig reactions with lactols. Nucleophilic additions to sugar lactones followed by lactol reductions. Nucleophilic additions to sugars containing enones. Transition metal mediated carbon monoxide insertions. Reactions involving anomeric carbenes. Reactions involving exoanomeric methylenes. References
Nucleophilic Sugar Substitutions
Introduction. C1 lithiated anomeric carbanions by direct metal exchange. C1 lithiated anomeric carbanions by reduction. C1 carbanions stabilized by sulfones, sulfoxides, carboxyl and nitro groups. References

Transition Metal Mediated C-Glycosidations
Introduction. Direct coupling of glycals with aryl groups. Coupling of substituted glycals with aryl groups. Coupling of &pgr;-allyl complexes of glycals. Mechanistic considerations. References

Anomeric Radicals
Introduction. Sources of anomeric radicals and stereochemical consequences. Anomeric couplings with radical acceptors. Intramolecular radical reactions. References

Rearrangements and Cycloadditions
Introduction. Rearrangements by substituent cleavage and recombination. Electrocyclic rearrangements involving glycals. Rearrangements from the 2-hydroxyl group. Biomolecular cycloadditions. Manipulations of C-Glycosides. References

Sugar Ring Formations
Introduction. Wittig reactions of lactols followed by ring closures. Addition of Grignard and organozinc reagents to lactols. Cyclization of suitably substituted polyols. Rearrangements. Cycloadditions. Other methods for the formation of sugar rings. References

Syntheses of C-Di and Trisaccharides
Introduction. Syntheses reported in 1983. Syntheses reported in 1984. Syntheses reported in 1985. Syntheses reported in 1986. Syntheses reported in 1987. Syntheses reported in 1988. Syntheses reported in 1989. Syntheses reported in 1990. Syntheses reported in 1991. Syntheses reported in 1992. Syntheses reported in 1993. Syntheses reported in 1994. Trends of the future. References. Index.