Convergent synthesis of polyhalogenated quinoline C-nucleosides as potential antiviral agents

JJ Chen, JC Drach, LB Townsend

Index: Chen, Jiong J.; Drach, John C.; Townsend, Leroy B. Journal of Organic Chemistry, 2003 , vol. 68, # 11 p. 4170 - 4178

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Citation Number: 26

Abstract

2, 5, 6-Trichloro-1-(β-d-ribofuranosyl) benzimidazole (TCRB) and 2-bromo-5, 6-dichloro-1-(β- d-ribofuranosyl) benzimidazole (BDCRB) are benzimidazole nucleosides that exhibit strong and selective anti-HCMV activity. We proposed to synthesize 2-halo-6, 7-dichloro-4-(β-d- ribofuranosyl) quinolines as 6+ 6 bicyclic analogues of TCRB. The synthesis used Wittig reactions in two key steps. The first Wittig reaction coupled a fully functionalized benzene ...