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■ Recent Advances in the Total Synthesis of Indolizidine Iminosugars

In Su Kim* and Young Hoon Jung*

*Department of Chemistry, University of Ulsan, Ulsan 680-749, Korea

Abstract

The importance of sugar-mimic glycosidase inhibitors in biochemistry, medicinal chemistry, and in the various aspects of life processes presents a challenge. The structural diversity of their multichiral architecture has long intrigued synthetic chemists to develop novel approaches to this class of compounds. Since glycosidase inhibitors have shown remarkable therapeutic potential in treating various metabolic diseases, an impressive number of synthetic routes to such compounds and their derivatives have been recently developed. This report highlights recent developments in the synthesis of indolizidine iminosugars. Different synthetic strategies have been used such as ring-closing metathesis, dihydroxylation, asymmetric epoxidation, [3,3]-sigmatropic rearrangement, desymmetrization, and amination. The potential application of our amination methodology that uses chlorosulfonyl isocyanate (CSI) for producing a variety of polyhydroxylated alkaloids will be presented.