Uracil and Adenine Nucleosides Having a 2',3'-Bromovinyl Structure: Highly Versatile Synthons for the Synthesis of 2'-C- and 3'-C-Branched 2',3'-Unsaturated Derivatives

Article abstract of DOI:10.1016/S0040-4020(01)90190-5

Preparation of 2'- and 3'-bromo derivatives of 2',3'-unsaturated uracil and adenine nucleosides has been carried out starting from the corresponding β-hydroxyselenides by way of bromination and successive selenoxide elimination.These compounds have been shown to serve as versatile synthons for the preparation of anti-HIV candidates, 2'-C- and 3'-C-branched 2',3'-unsaturated nucleosides, through palladium-catalyzed cross-coupling and halogen-lithium exchange reactions. Key Words: β-hydroxyselenide; bromovinyl structure; branched-sugar nucleoside; anti-HIV agent; 2',3'-unsaturated nucleoside.