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Synthesis 2011(2): 337-341  
DOI: 10.1055/s-0030-1258369
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

CeCl3˙7H2O: A Versatile and Efficient Reagent for the Synthesis of C-Pyrrolyl Glycosides

Basi V. Subba Reddy*, Ruchi Jain, Kudikyala Bhargavi, Manisha Swain, Jhillu S. Yadav
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: basireddy@iict.res.in;
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Publikationsverlauf

Received 1 November 2010
Publikationsdatum:
17. Dezember 2010 (online)

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Abstract

1,3-Diketones and β-oxo esters undergo smooth coupling with d-glucosamine in the presence of 25 mol% CeCl3˙7H2O in water at 80 ˚C to furnish C-pyrrolyl glycosides in good to high yields. The reaction of cyclic diketones such as dimedone with d-glucosamine affords the corresponding 2-(3,4-dihydroxytetrahydrofuran-2-yl)-6,7-dihydro-1H-indol-4(5H)-one derivatives. These dihydroxy derivatives are directly converted into acetates using acetic anhydride and 4-(dimethylamino)pyridine. The use of readily available CeCl3˙7H2O makes this procedure quite simple, convenient and practical.

Key words

C-pyrrolyl glycosides - 1,3-diones - glucosamine - cerium(III) salts

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