Synthesis of modified polyoxins by reaction of uridine-5′-aldehyde with trimethylsilyl cyanide and amino acids

Abstract

The synthesis of six modified polyoxin derivatives containing an alkyl amino group replacing the peptide bond has been accomplished, in a one pot reaction, by condensation of 2′,3′-O-isopropylideneuridine-5′-aldehyde with trimethylsily cyanide, boron trifluoride etherate and an amino acid, in methanol. The reaction affords stereoselectively the diastereoisomer having at O-5′ the same absolute configuration as the natural polyoxins.