Enantiospecific total synthesis of (-)-polyoxamic acid using 2,3-aziridino-gamma-lactone methodology.
The non-natural enantiomer of polyoxamic acid was synthesized in six steps from 2,3-aziridino-gamma-lactone 7 with an overall yield of 10%. The key step of the strategy is a deprotection-protection sequence on the nitrogen atom of the aziridine ring required for aziridine activation toward nucleophilic ring opening.
Tarrade
Aurélie
A
Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, F-91198 Gif-sur-Yvette Cedex, France.
Dauban
Philippe
P
Dodd
Robert H
RH
D001383:Azetidinecarboxylic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D007783:Lactones / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism
C482827:2,3-aziridino-gamma-lactone; D007783:Lactones; C010624:polyoximic acid; D001383:Azetidinecarboxylic Acid