Abstract
Two strategies for the enantioselective synthesis of some isoxazolidinyl nucleosides, as potential antiviral drugs, are reported. In particular, a one-step approach based on 1,3-dipolar cycloaddition with vinyl nucleobases and a two-step methodology based on the Vorbruggen nucleosidation have been exploited in the preparation of 4'-aza-2',3'-dideoxynucleoside analogues containing uracil, 5-fluorouracil, thymine and cytosine.
Highlights
Derivatives of natural nucleic acids play an important role in current chemotherapy as potent and selective antiviral agents in AIDS therapy
The design of novel “ribose” rings has resulted in the discovery of effective biological agents; promising results have been obtained from a new generation of nucleoside analogues where the furanose ring has been replaced by an alternative carbo- or heterocyclic ring
The results show that the two-step procedure, based on the 1,3-dipolar cycloaddition of the chiral nitrone 4 with vinyl acetate and the subsequent Vorbrüggen nucleosidation, leads to clearly better yields
Summary
Derivatives of natural nucleic acids play an important role in current chemotherapy as potent and selective antiviral agents in AIDS therapy. A series of new compounds, endowed with relevant biological activity, originate from chemical modifications of the nucleic acid fragments at the level of the sugar moiety and/or the heterocyclic base. Derivatives of natural nucleic acids play an important role in current chemotherapy as potent and selective antiviral agents in AIDS therapy.. A series of new compounds, endowed with relevant biological activity, originate from chemical modifications of the nucleic acid fragments at the level of the sugar moiety and/or the heterocyclic base. In this context, the design of novel “ribose” rings has resulted in the discovery of effective biological agents; promising results have been obtained from a new generation of nucleoside analogues where the furanose ring has been replaced by an alternative carbo- or heterocyclic ring.. The design of novel “ribose” rings has resulted in the discovery of effective biological agents; promising results have been obtained from a new generation of nucleoside analogues where the furanose ring has been replaced by an alternative carbo- or heterocyclic ring. In particular, isoxazolidinyl nucleosides have been synthesized recently in order to investigate their pharmacological activities. Page159
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