Straightforward synthesis of labeled and unlabeled pyrimidine d4Ns via 2 ',3 '-diyne seco analogues through olefin metathesis reactions

I Gillaizeau, I M Lagoja, Steven Patrick Nolan, V Aucagne, J Rozenski, P Herdewijn, L A Agrofoglio

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

The synthesis of dideoxynucleosides (ddNs) or didehydro-dideoxynucleosides (d4Ns) from nucleosides has been extensively reviewed. While previously described methods are based on the modification of the 2'- and/or T-OH group of the intact ribose moiety, the use of a ring-closing metathesis (RCM) for the formation of the unsaturated cyclic system of nucleosides could be a straightforward approach to the d4Ns. Thus, as part of our drug labeling program, this paper reports a straightforward synthesis of 2',3'-didehydro-2',3'-dideoxyuridine (d4U) and [1',2',3',4',5'-C-13(5),6-C-13,1,3-N-15(2)]d4T using the RCM protocol. This paper discusses the preparation of nucleoside dienes and the activity of ruthenium-based metathesis catalysts. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

Original languageEnglish
Pages (from-to)666-671
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number4
Publication statusPublished - Feb 2003

Keywords

  • ring-closing metathesis
  • alkynes
  • nucleosides
  • isotopic labeling
  • RING-CLOSING METATHESIS
  • ACID RELATED-COMPOUNDS
  • CIS-VICINAL DIOLS
  • 2',3'-DIDEOXYNUCLEOSIDE ANALOGS
  • NUCLEOSIDE 2',3'-DIMESYLATES
  • ENANTIOSELECTIVE SYNTHESIS
  • STEREOSELECTIVE SYNTHESIS
  • CARBOCYCLIC NUCLEOSIDES
  • EFFICIENT PREPARATION
  • 2',3'-DIDEHYDRO-2',3'-DIDEOXYNUCLEOSIDES

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