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Abstract
AbstractThe synthesis of two polyhydroxylated indolizidines as potenticial glycosidase inhibitors is reported. The piperidine ring was formed by an intramolecular Mannich‐type reaction between ethyl trans‐4‐oxo‐2‐butenoate and the two β‐amino ketones (–)‐1‐(2‐methyl‐1,3‐dioxan‐2‐yl)propan‐2‐amine and(+)‐1‐(benzyloxymethyl)‐2‐(2‐methyl‐1,3‐dioxan‐2‐yl)ethylamine. The synthesis of this amine was performed in eight steps from L‐aspartic acid. The key steps of the formation of the framework involved dihydroxylation, nucleophilic substitution, and reduction. The last hydroxy group was introduced by hydrolysis of the acetal moiety followed by reduction of the resulting ketone. The inhibitory properties of the two synthesized indolizidines were evaluated against a variety of commercial glycosidases. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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