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

✍ Scribed by Mohammad Abrar Alam; Amit Kumar; Yashwant D. Vankar

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
306 KB
Volume
2008
Category
Article
ISSN
1434-193X

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✦ Synopsis

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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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