Synthesis of Modified Polyoxins by Reaction of Uridine-5'-aldehyde with Trimethylsilyl Cyanide and Amino Acids

Article abstract of DOI:10.1055/s-1987-28141

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