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Synthesis 2005(20): 3531-3534  
DOI: 10.1055/s-2005-918489
PAPER
© Georg Thieme Verlag Stuttgart · New York

First Synthesis of N-Indigoglycosides - Analogues of Cancerostatic Akashines

Martin Hein*a, Dirk Michalikb, Peter Langer*a,b
a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
b Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. (IfOK), Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Further Information

Publication History

Received 9 October 2005
Publication Date:
24 November 2005 (online)

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Abstract

The first and surprisingly simple synthesis of N-indigoglycosides has been accomplished based on glycosylation of N-benzylindigo with tri-O-pivaloyl-α-l-rhamnosyl trichloroacetimidate and subsequent rearrangement of the O- into the N-glycoside. N-Indigoglycosides are of considerable pharmacological relevance and occur in cancerostatic natural akashines.

Key words

indigo - N-heterocycles - rearrangements - regioselectivity

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