5-Hydroxy [1, 2] oxazinan-3-ones as potential carbapenem and D-ala-D-ala surrogates

S Wolfe, C Akuche, S Ro, MC Wilson…

Index: Wolfe, Saul; Akuche, Christiana; Ro, Stephen; Wilson, Marie-Claire; Kim, Chan-Kyung; Shi, Zheng Canadian Journal of Chemistry, 2003 , vol. 81, # 8 p. 915 - 936

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Citation Number: 16

Abstract

The title compounds are amino acids whose nitrogen atom is enclosed in a six-membered cyclic hydroxamate bearing a C5-hydroxyl group. They belong to a proposed new family of antibacterial agents targeted to the penicillin receptor. The glycine and alanine members of the family have been synthesized, as racemates, in seven steps from the four-carbon synthon diketene and the tert-butyl esters of N-hydroxyglycine and N-hydroxyalanine. ...