TOTALLY SYNTHETIC ANALOGUES OF SIASTATIN B

II. OPTICALLY ACTIVE PIPERIDINE DERIVATIVES HAVING TRIFLUOROACETAMIDE AND HYDROXYACETAMIDE GROUPS AT C-2

Abstract

Siastatin B analogues, optically active 2-(trifluoroacetamide)-3, 4, 5-trihydroxypiperidines having nitromethyl, aminomethyl and carboxyl branched groups at C-5, and (+)-(2R, 3R, 4R, 5R)-5-(aminomethyl)-3, 4, 5-trihydroxy-2-(hydroxyacetamido)piperidine have been obtained total synthetically from D-ribono-1, 4-lactone. Some analogues have inhibitory activity against some glycosidases, and (+)-(2R, 3R, 4R, 5R)-2-(trifluoroacetamido)-3, 4, 5-trihydroxypiperidine-5-carboxylic acid showed a marked inhibitory activity against β-glucuronidase.