The chemistry and biochemistry of C-nucleosides and C-arylglycosides.

This chapter reviews recent advances in the chemistry and biochemistry of C-nucleosides, the literature concerning C-arylglycoside (i.e., nonnitrogen heterocyclic C-nucleoside) antibiotics, and recent significant advances in the synthesis of C-nucleosides and C-glycosides. It also discusses biological test data and data that are relevant to structure–activity relationships. Modification of readily available natural C-nucleosides is an attractive route to new C-nucleoside analogs and derivatives, because one starting material often possesses much of the desired functionality and chiral properties. The chapter illustrates this approach with examples. The most frequently used strategy for C-nucleoside synthesis involves the construction of a heterocyclic aglycone from the C-1 substituent of a functionalized sugar intermediate.