New Synthesis of Penta-<i>N</i>,<i>O</i>-acetyl-<scp>Dl</scp>-validamine and Pseudo-2-amino-2-deoxy-α-<scp>Dl</scp>-mannopyranose, and Their Uronate Analogs

Abstract

Abstract Treatment of the hydroxy lactone derived from (±)-endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid with hydrogen bromide–acetic acid, followed by esterification, gave 48% of ethyl Dl-(1,3,5/2,4)-5-bromo-2,3,4-trihydroxy-1-cyclohexanecarboxylate, from which Dl-validamine and pseudo-2-amino-2-deoxy-α-Dl-mannopyranose, and their uronate analogs have been synthesized as the totally acetylated derivatives.