An Improved Synthesis of N-Hydroxyamino Acids and Their Esters Using (Z)-2-Furaldehyde Oxime

Abstract

A series of N-hydroxyamino acids and their esters (9a, b, d—k) coupled with N-hydroxygly-cinamide (9c) were synthesized through facile preparations of N-furfurylidenealkoxy (and hydroxy) carbonylalkylamine N-oxides (7a, b, d—g) and N-furfurylidenecarbamoylmethylamine N-oxide (7c) followed by hydrolysis. The method was applied to the syntheses of emimycin (1) and hadacidin monosodium salt (2b). © 1986, The Pharmaceutical Society of Japan. All rights reserved.