Fluorinated methylenecyclopropane analogues of nucleosides. Synthesis and antiviral activity of (Z)-and (E)-9-{[(2-fluoromethyl-2-hydroxymethyl)-cyclopropylidene] …

…, MN Prichard, BE Korba, JC Drach, J Zemlicka

Index: Li, Chengwei; Prichard, Mark N.; Korba, Brent E.; Drach, John C.; Zemlicka, Jiri Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 5 p. 2148 - 2155

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Citation Number: 13

Abstract

Synthesis and antiviral activity of the title fluoromethylenecyclopropane analogues 15a, 15b, 16a, and 16b is described. Methylenecyclopropane carboxylate was first transformed to 2, 2- bis-hydroxymethylmethylenecyclopropane. Selective monoacetylation followed by introduction of fluorine gave 2-acetoxymethyl-2-fluoromethylmethylenecyclopropane as the key intermediate. The synthesis of analogues 15a, 15b, 16a, and 16b then followed ...