Stereocontrolled Synthesis and Biological Evaluation of Novel Carbocyclic Nucleosides Analogues of Neplanocin F and Abacavir

Abstract

Starting from a readily available building block, two straightforward diastereoselective approaches to functionalized 3′-methyl-branched carbocyclic nucleoside analogues of neplanocin F and abacavir bearing different purine bases are described. The key steps are a regioselective allylic hydroxylation in the first approach and a ring opening of a cyclic carbonate for the second one, affording allylic alcohols as carbasugar intermediates. In both cases, the carbasugars thus synthesized are then coupled with different purine bases.

Key words

stereoselective synthesis - nucleosides - Mitsunobu ­reaction - purine - carbocyclic nucleoside

References and Notes

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