Novel anomeric spironucleosides and 1'-cyano-2',3'-didehydro-2',3'-dideoxyuridine, a structural analogue of known anti-HIV agent, were prepared by nucleophilic addition of organolithium reagents to 1'-cyano-2'deoxy- and 1'-cyano-2'-deoxy-2'beta-bromouridine derivatives, respectively. The yield and distribution of products depended on the reaction conditions, whichwere studied in detail. Although none of the compounds exhibited antiviral activit, twocompounds displayed cytostatic activity against both murine leukemia and human T-lymphocyte cells.

Novel anomeric spironucleosides and 1′-cyano-2′,3′- didehydro-2′,3′-dideoxyuridine, a structural analogue of known anti-HIV agents, were prepared by nucleophilic addition of organolithium reagents to 1′-cyano-2′-deoxy- and 1′-cyano-2′-deoxy- 2′$\beta$-bromo-uridine derivatives, respectively. The yield and distribution of products depended on the reaction conditions, which were studied in detail. Although none of the compounds exhibited antiviral activity, two compounds displayed cytostatic activity against both murine leukemia and human T-lymphocyte cells.

The thermal reaction (at 140°C) of various 1′,2′-didehydro- 2′-deoxynucleosides afforded the corresponding furanyl nucleosides in good yields. The reaction kinetics were monitored by 1H NMR and the mechanism in terms of 'four-center complex fission' is discussed. © 2004 Elsevier Ltd. All rights reserved.