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Abstract
AbstractD‐Glucose‐derived aziridine‐2‐carboxylate 1 was converted into α‐amino aldehyde 7, which, after Wittig olefination, asymmetric dihydroxylation, hydrogenation followed byLiAlH4 reduction, and N‐Cbz protection, afforded two diastereomeric pyrrolidines 11a and 11b with sugar appendages. Removal of the 1,2‐acetonide functionality in 11a/11b and reductive amination gave the pentahydroxyindolizidine alkaloids 6g and 6h, respectively, with (S) absolute configurations at the ring junctions. The glycosidase inhibitory activities of these compounds were studied. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
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