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Synthesis 2003(16): 2473-2478  
DOI: 10.1055/s-2003-42423
PAPER
© Georg Thieme Verlag Stuttgart · New York

Simple Total Syntheses of (+)-Castanospermine and (+)-6-Epicastanospermine Using Indium-Mediated Allylation

Jin Hyo Kim, Woo Duck Seo, Jin Hwan Lee, Byong Won Lee, Ki Hun Park*
Division of Applied Life Science, BK21 Programs, Department of Agricultural Chemistry, Gyeongsang National University, Jinju 660-701, Korea
Fax: +82(55)7570178; e-Mail: khpark@gshp.gsnu.ac.kr;
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Publication History

Received 7 July 2003
Publication Date:
07 October 2003 (online)

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Abstract

The indium-mediated allylation of α-aminoaldehyde 3 from d-glucono-δ-lactone provided the syn-aminoalcohol with excellent diastereoselectivity. syn-Aminoalcohol was easily applied to the total syntheses of the potent glycosidase inhibitors; (+)-castanospermine and (+)-6-epicastanospermine.

Keywords

(+)-castanospermine - (+)-6-epicastanospermine - indium-mediated allylation - (+)-cinchonine - glycosidase inhibitor