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Beilstein J Org Chem. 2011;7:1228-33. doi: 10.3762/bjoc.7.143. Epub 2011 Sep 6.

Selectivity in C-alkylation of dianions of protected 6-methyluridine.

Author information

  • 1Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France.

Abstract

A regioselective synthesis of 6-ω-alkenyluridines 3, precursors of potent antiviral and antitumor cyclonucleosides 5, is described. While ω-alkenyl halides do not alkylate 6-lithiouridine, compounds 3 were prepared in a regioselective manner by sequential treatment of 6-methyluridine 2 with LTMP or LDA (4 equiv) in THF at -30 °C followed by alkylation with ω-alkenyl bromides.

KEYWORDS:

6-ω-alkenyluridines; C6-alkylation; cyclonucleosides; lithiations

PMID:
21977207
[PubMed]
PMCID:
PMC3182432
Free PMC Article

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