Stereoselective synthesis of 3,4,5,6-tetrahydroxycyclohexyl b-amino acid derivatives

Abstract

Stereoselective syntheses of racemic (1S,2R,3R,4R,5S,6R)- and (1S,2R,3R,4S,5S,6R)-3,4,5,6-tetrahydroxy derivatives of 2-aminocyclohexanecarboxylic acid have been achieved by a stereospecific Diels–Alder reaction between furan and maleic anhydride, a Curtius rearrangement and hydroxylation reactions.