Divergent synthesis and biological evaluation of carbocyclic α-, iso- and 3′-epi-nucleosides and their lipophilic nucleotide prodrugs

Olaf R. Ludek, Tobias Krämer, Jan Balzarini, Chris Meier

Research output: Contribution to journalArticle

24 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1313-1324
Number of pages12
JournalSynthesis
Issue number8
DOIs
Publication statusPublished - Apr 2006

Keywords

  • Carbocycles
  • Hydroborations
  • Mitsunobu reaction
  • Nucleosides
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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