☆ 4.5 Article

Total Synthesis of L-(+)-Swainsonine and Other Indolizidine Azasugars from D-Glucose

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2008)

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Volume 2008, Issue 29, Pages 4972-4980

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/ejoc.200800649

Keywords

Nitrogen heterocycles; Azasugars; Epoxides; Nucleophilic substitution

Categories

Chemistry, Organic

Funding

Department of Science and Technology, New Delhi [SR/S1/RFOC-04/2006]
C.S.I.R., New Delhi

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Abstract

A total synthesis of L-(+)-swainsonine, a potent and specific inhibitor of naringinase, along with the syntheses of six unnatural indolizidine azasugars are reported by starting from D-glucose. L-(+)-Swainsonine was synthesized in 14 steps in 17% overall yield. Further, two of the indolizidine analogues were found to be good glycosidase inhibitors at micromolar concentrations. In all of these syntheses, the key step was an intramolecular S(N)2 reaction. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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