Tetrahedron p. 1371 - 1390 (1993)
Update date:2022-07-30
Topics:
Haraguchi, Kazuhiro
Itoh, Yoshiharu
Tanaka, Hiromichi
Akita, Mitsuhiro
Miyasaka, Tadashi
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.
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