Tetrahedron

A new alkylation–elimination method for synthesis of antiviral fluoromethylenecyclopropane analogues of nucleosides

S Zhou, J Zemlicka

Index: Zhou, Shaoman; Zemlicka, Jiri Tetrahedron, 2005 , vol. 61, # 30 p. 7112 - 7116

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Citation Number: 21

Abstract

A new method for the synthesis of fluoromethylenecyclopropane nucleosides by alkylation– elimination procedure is described. Fluorination of methylenecyclopropane carboxylate gave fluoroester. Treatment of with phenylselenenyl bromide afforded the desired ethyl (E)-2- bromomethyl-1-fluoro-2-phenylselenenylcyclopropane-1-carboxylate in 85% yield. DIBALH reduction of gave, which after acetylation to was reacted with 2-amino-6-chloropurine to ...