Title: Synthesis of 6-aryl-2 '-deoxyuridine nucleosides via a Liebeskind cross-coupling methodology
Authors: K√∂gler, Martin ×
De Jonghe, Steven
Herdewijn, Piet #
Issue Date: Jan-2012
Publisher: Pergamon Press
Series Title: Tetrahedron Letters vol:53 issue:2 pages:253-255
Abstract: Hitherto, the synthesis of 6-substituted 2'-deoxyuridine nucleoside analogues via Pd-catalyzed Suzuki cross-coupling reaction was hampered by the instability of the TIPDS-protected precursor 6-iodo-2'-deoxyuridine 1 in alkaline media due to cleavage of the glycosidic bond. Herein, the successful application of the Liebeskind reaction under base-free conditions is reported. This method comprises of the stoichiometric use of copper thiophene carboxylate (CuTC) as co-reagent at slightly elevated temperatures. Fluoride-mediated desilylation and Yoshikawa-phosphorylation afforded the nucleotide analogues 4b-c, 4e, and 4i. (C) 2011 Elsevier Ltd. All rights reserved.
ISSN: 0040-4039
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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