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Synthesis 1987; 1987(11): 978-981
DOI: 10.1055/s-1987-28141
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Synthesis of Modified Polyoxins by Reaction of Uridine-5′-aldehyde with Trimethylsilyl Cyanide and Amino Acids

José Fiandor* , María-Teresa García-López, Federico G. De Las Heras, Paloma P. Méndez-Castrillón
  • *Instituto de Química Médica (C.S.I.C.), Juan de la Cierva 3, E-28006 Madrid, Spain
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Publication Date:
12 September 2002 (online)

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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.