ACYCLIC STEREOCONTROLLED SYNTHESIS OF (-)-DETOXININE

Article abstract of DOI:10.1016/S0040-4039(01)90201-1

Allylic oxidation of (2S)-N-t-butoxycarbonyl-2-amino-4-pentenoic acid methyl ester afforded, stereoselectively, a (2S,3R)-2-amino-3-hydroxyl derivative, which was converted to the unusual amino acid (-)-detoxinine via a chelation controlled aldol condensation followed by a pyrrolidine ring formation.