Total Synthesis of 6-Deoxy-6-aminoheptopyranuronic Acid Derivatives

Article abstract of DOI:10.1021/jo00023a015

Two enantio couples of terminal C-glycoyranosyl α-amino acids, namely the aminopyranuronic acid, L-9, D-9 and L-10, D-10, hve been synthesized from serine-derived pair L-2, D-2 by exploiting enantiomerically pure butenolide intermediates 3 and 4.The key synthetic steps involved the sequential antiselective cis dihydroxylation of the butenolide double bond and the clean furaose-to-pyranose ring expansion to construct the sugar skeleton with the proper stereochemistry.In our best performance, homogeneous L-9 was prepared from L-2 in four steps and 10 reactions in 20percent overall yield.