Total synthesis of 6-deoxy-6-aminoheptopyranuronic acid derivatives

G Casiraghi, L Colombo, G Rassu…

Index: Casiraghi, Giovanni; Colombo, Lino; Rassu, Gloria; Spanu, Pietro Journal of Organic Chemistry, 1991 , vol. 56, # 23 p. 6523 - 6527

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Citation Number: 86

Abstract

Two enantio couples of terminal C-glycopyranosyl a-amino acids, namely the aminopyranuronic acids L-9, D-9 and L-10, D-10, have been synthesized from the 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 furanose-to-pyranose ring expansion to construct ...