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Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies |
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| Authors: | Franck Amblard Raymond F Schinazi |
| Institution: | a ICOA UMR CNRS 6005, BP 6759, 45067 Orleans Cedex 2, France b Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA c Veterans Affairs Medical Center and Lab. Biochem. Pharmacol., Emory University, Atlanta, GA 30033, USA |
| Abstract: | Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. |
| Keywords: | Cross-metathesis Acyclonucleosides Suzuki-Miyaura Pd(0) |
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