The Chemistry of C-Glycosides (Tetrahedron Organic Chemistry)

Front Cover......Page 1
The Chemistry of C-Glycosides......Page 4
Copyright Page......Page 5
Contents......Page 6
Acknowledgements......Page 12
Abbreviations......Page 14
1.1 Definition and Nomenclature of C-Glycosides......Page 16
1.2 O-Glycosides vs. C-Glycosides: Comparisons of Physical Properties, Anomeric Effects, H-Bonding Abilities, Stabilities and Conformations......Page 19
1.3 Naturally Occurring C-Glycosides......Page 22
1.4 C-Glycosides as Stable Pharmacophores......Page 25
1.6 References......Page 37
2.1 Anomeric Activating Groups and Stereoselectivity......Page 44
2.2 Cyanation Reactions......Page 45
2.3 Alkylation, Allenylation, Allylation and Alkynation Reactions......Page 57
2.4 Arylation Reactions......Page 86
2.5 Reactions with Enol Ethers, Silylenol Ethers and Enamines......Page 104
2.6 Nitroalkylation Reactions......Page 113
2.7 Reactions with Allylic Ethers......Page 116
2.8 Wittig Reactions with Lactols......Page 119
2.9 Nucleophilic Additions to Sugar Lactones Followed by Lactol Reductions......Page 126
2.10 Nucleophilic Additions to Sugars Containing Enones......Page 131
2.11 Transition Metal Mediated Carbon Monoxide Insertions......Page 134
2.12 Reactions Involving Anomeric Carbenes......Page 138
2.13 Reactions Involving Exoanomeric Methylenes......Page 140
2.14 References......Page 143
3. Introduction......Page 148
3.1 C1 Lithiated Anomeric Carbanions by Direct Metal Exchange......Page 149
3.2 C1 Lithiated Anomeric Carbanions by Reduction......Page 155
3.3 C1 Carbanions Stabilized by Sulfones, Sulfides, Sulfoxides, Carboxyl and Nitro Groups......Page 158
3.4 References......Page 167
4.1 Direct Coupling of Glycals and Aryl Groups......Page 170
4.2 Coupling of Substituted Glycals with Aryl Groups......Page 179
4.3 Coupling of Pi-Allyl Complexes of Glycals......Page 182
4.4 Mechanistic Considerations......Page 186
4.5 References......Page 188
5.1 Sources of Anomeric Radicals and Stereochemical Consequences......Page 190
5.2 Anomeric Couplings with Radical Acceptors......Page 195
5.3 Intramolecular Radical Reactions......Page 207
5.4 References......Page 210
6. Introduction......Page 212
6.1 Rearrangements by Substituent Cleavage and Recombination......Page 213
6.2 Electrocyclic Rearrangements Involving Glycals......Page 216
6.3 Rearrangements from the 2-Hydroxyl Group......Page 219
6.5 Manipulations of C-Glycosides......Page 221
6.6 References......Page 225
7. Introduction......Page 226
7.1 Wittig Reactions of Lactols Followed by Ring Closures......Page 227
7.2 Addition of Grignard and Organozinc Reagents to Lactols......Page 234
7.3 Cyclization of Suitably Substituted Polyols......Page 235
7.4 Rearrangements......Page 241
7.5 Cycloadditions......Page 245
7.6 Other Methods for the Formation of Sugar Rings......Page 248
7.7 References......Page 249
8.1 Syntheses Reported in 1983......Page 252
8.2 Syntheses Reported in 1984......Page 253
8.3 Syntheses Reported in 1985......Page 255
8.4 Syntheses Reported in 1986......Page 257
8.5 Syntheses Reported in 1987......Page 259
8.6 Syntheses Reported in 1988......Page 260
8.7 Syntheses Reported in 1989......Page 262
8.8 Syntheses Reported in 1990......Page 267
8.9 Syntheses Reported in 1991......Page 269
8.10 Syntheses Reported in 1992......Page 274
8.11 Syntheses Reported in 1993......Page 281
8.12 Syntheses Reported in 1994......Page 287
8.13 Trends of the Future......Page 289
8.14 References......Page 291
Index......Page 294
Authors' Biographies......Page 306