Synthetic studies towards peptidyl nucleoside antibiotics: first synthesis of a polyoxamic acid derivative enabling direct coupling with α-amino acid esters

Abstract

The reaction of the Mukaiyama’s aldehyde-derived N- benzyl imine with an hydroxyketene equivalent followed by exposure of the resulting α-hydroxy β-lactam to NaOCl and 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO) provides a novel α-amino acid N-carboxy anhydride formally derived from polyoxamic acid.