Abstract
Conformationally restricted 2′-C-azido-, hydroxy- and fluoromethyl-carbanucleosides 4b-f were efficiently synthesized via the stereoselective conversion of ketone 7 to epoxide 14, followed by the stereoselective opening of the epoxide with nucleophiles (OAc, N 3, and F), while the corresponding 2′-C-methyl-carbanucleoside 4a was synthesized via the stereoselective Grignard reaction of ketone 7 with methylmagnesium iodide as a key step. All the final nucleosides 4a-f were assayed for anti-HCV activity, but showed neither significant anti-HCV activity nor cytotoxicity in a cell-based replicon assay.
Original language | English |
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Pages (from-to) | 1253-1261 |
Number of pages | 9 |
Journal | Tetrahedron |
Volume | 68 |
Issue number | 4 |
DOIs | |
State | Published - 28 Jan 2012 |
Keywords
- Anti-HCV activity
- Carbocyclic nucleosides
- Cyclic sulfate
- Stereoselective epoxidation
- Sulfur ylide