Abstract
This chapter focuses on the asymmetric chemical synthesis of carbocyclic analogues of nucleosides, especially on five-membered ring derivatives, even if the preparation of analogues based on other ring sizes is summarized. Although the key synthetic methods developed before 1998 are described, the work reported since the last review on the topic is highlighted. Current methods used for the introduction of the heterocyclic base on the carbasugar, including unusual or C-linked bases, are reported first. The asymmetric synthesis of cyclopentyl carbocyclic analogues of nucleosides is reviewed second. From methods using a resolved cyclopentene building block as the starting material to catalytic enantioselective syntheses, various leading strategies are reported. Finally, the synthesis of fluorinated, cyclohexylic, cyclobutylic, and cyclopropylic carbanucleosides is summarized. Many examples of palladium-catalyzed introduction of nucleobases to functionalized cyclopentenes are described in this chapter.