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Synthesis 2006(8): 1313-1324
DOI: 10.1055/s-2006-926411
DOI: 10.1055/s-2006-926411
PAPER
© Georg Thieme Verlag Stuttgart · New York
Divergent Synthesis and Biological Evaluation of Carbocyclic α-, iso- and 3′-epi-Nucleosides and their Lipophilic Nucleotide Prodrugs
Further Information
Received
26 September 2005
Publication Date:
27 March 2006 (online)
Publication History
Publication Date:
27 March 2006 (online)
Abstract
A new divergent approach towards carbocyclic α-, iso- and 3′-epi-nucleosides starting from enantiomerically pure (1S,2R)-2-benzyloxymethylcyclopent-3-enol (5) is described. In the key step, isomeric cyclopentanols were condensed with a N3-protected pyrimidine nucleobase using a modified Mitsunobu protocol. Moreover, the conversion into the cycloSal-pronucleotides and the effect of the orientation of the nucleobase on anti-HIV activity are reported.
Key words
stereoselective synthesis - hydroborations - carbocycles - nucleosides - Mitsunobu reaction
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