2-(Acyloxy) ethylphosphonate analogues of prenyl pyrophosphates: synthesis and biological characterization

DM Cermak, DF Wiemer, K Lewis, RJ Hohl

Index: Cermak, Diana M.; Wiemer, David F.; Lewis, Kriste; Hohl, Raymond J. Bioorganic and Medicinal Chemistry, 2000 , vol. 8, # 12 p. 2729 - 2737

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Citation Number: 22

Abstract

2-(Acyloxy) ethylphosphonate analogues of geranyl, farnesyl, and geranylgeranyl pyrophosphate have been prepared. Horner–Wadsworth–Emmons condensation of different terpene aldehydes with an unsymmetrical bisphosphonate was the key step in syntheses of the phosphonates bearing α, β-unsaturated acyloxy groups. After preparation of the respective phosphonic acids through reaction with TMSBr, both acids and esters were ...