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Introduction 6729 2. C-Nucleosides in Chemical Biology 6730 2.1. Extension of the Genetic Alphabet 6730 2.1.1. Artificial Base-Pairs Based on Hydrogen Bonding 6731 2.1.2. Artificial Base-Pairs Based on Hydrophobic Interactions 6733 2.1.3. Artificial Base-Pairs Based on Metal Bridges 6735 2.1.4. Conclusions and Outlook of Artificial Base-Pairs 6736 2.2. Other Applications in Chemical Biology 6736 3. Medicinal Chemistry of C-Nucleosides 6736 3.1. Natural C-Nucleosides 6736 3.2. Mechanism-Based Biologically Active C-Nucleosides 6737 3.2.1. Inhibitors of Nucleolytic Enzymes 6737 3.2.2. Inhibitors of Oxidoreductases 6738 3.2.3. Conclusions and Outlook in Medicinal Chemistry 6738 4. Synthesis of C-Nucleosides 6738 4.1. Construction of an Aglycon Unit upon a Carbohydrate Moiety 6738 4.1.1. Introduction of the Nitrile Group and its Heterocyclizations 6738 4.1.2. Wittig-Type Reactions 6740 4.1.3. Cycloadditions 6741 4.1.4. Other Methods for the Construction of the Aglycon Unit 6744 4.2. Construction of a Carbohydrate Moiety upon an Aglycon Unit 6744 4.3. Direct Coupling of a Carbohydrate Moiety with a Preformed Aglycon Unit 6749 4.3.1. Nucleophilic Addition to the Aldehyde Function of a Carbohydrate 6749 4.3.2. Nucleophilic Addition to 1,2-Anhydrofuranoses 6750 4.3.3. Couplings of Nucleophiles with Halogenoses 6750 4.3.4. Nucleophilic Addition to Furanolactones 6751 4.3.5. Heck Coupling 6752 4.3.6. Lewis Acids-Mediated Electrophilic Substitutions 6753 4.4. Modification of the Existing C-Nucleosides 6754 4.5. Modular Approaches 6757 5. Conclusions 6759 6. Acknowledgments 6759 7. References 6759

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Regioselective Suzuki-Miyaura reaction of 8-bromo-6-iodo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine with phenylboronic acid gave 8-bromo-6-phenylpurine derivative that was used for cross-coupling reactions (with PhB(OH)2, Me3Al, Et3Al, BnZnCl) or nucleophilic substitutions (with NaOH, NaOMe, NH3, NHMe2 or thiourea). A series of 8-X-substituted 6-phenyl-9-(β-D-ribofuranosyl)purines (X = Ph, Me, Et, Bn, OH, OMe, NH2, NMe2, SH) was prepared in this way directly or after deprotection. None of the title nucleosides exhibited any considerable cytostatic activity.