Efficient synthesis of 4′-cyclopropylated carbovir analogues with use of ring-closing metathesis from glycolate

LJ Liu, JC Yoo, JH Hong

Index: Liu, Lian Jin; Yoo, Jin Cheol; Hong, Joon Hee Nucleosides, Nucleotides and Nucleic Acids, 2008 , vol. 27, # 10-11 p. 1186 - 1196

Full Text: HTML

Citation Number: 6

Abstract

The first synthetic route of novel 4′-cyclopropylated carbovir analgues is described. The construction of cyclopropylated quaternary carbon at 4′-position of carbocyclic nucleosides was successfully made via sequential Johnson's orthoester rearrangement and ring-closing metathesis (RCM) starting from ethyl glycolate. Synthesized compounds 15 and 16 showed moderate antiviral activity without any cytotoxicity up to 100 μmol.