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Modular Synthesis of 4-aryl- and 4-amino-substituted benzene C-2?-Deoxyribonucleosides
A modular methodology for the syntheses of various 4-substituted-phenyl C-2?-deoxyribonucleosides has been developed. Coupling of toluoylated halogenose 1 with 4-bromophenylmagnesium bromide afforded the desired bis(toluoyl)-protected 1beta-(4-bromophenyl)-1,2-dideoxyribofuranose 2a, which was deprotected under Zemplen conditions to give the unprotected 1beta-(4-bromophenyl)-1,2-dideoxyribofuranosc 3, and reprotected to give the bis(tert-butyldimethylsilyl)-protected 1beta-(4-bromophenyl)-1,2- dideoxyribofuranose 4. Alternatively, addition of 1-lithio-4-bromobenzene on tert-butyldimethylsilyl-protected lactone 5, followed by reduction of the hemiketal 6, also gave bis(tert-butyldimethylsilyl)-protected bromophenyl nucleoside 4. Intermediates 2a and 4 were then subjected to a series of palladium-catalyzed cross-coupling reactions, aminations, and C-H activation to give 1beta-[4-(aryl-, alkyl-, or amino)phenyl]-1,2-dideoxyribofuranoses 8a-n after deprotection. Finally, other types of 4-arylphenyl C-nucleosides 8o-u were prepared directly by aqueous-phase Suzuki cross-coupling reactions of unprotected 3 with boronic acids under microwave irradiation.
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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI