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
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