Synthesis of Modified Polyoxins by Reaction of Uridine-5′-aldehyde with Trimethylsilyl Cyanide and Amino Acids
- 1 January 1987
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1987 (11) , 978-981
- https://doi.org/10.1055/s-1987-28141
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.Keywords
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