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Synthesis 2005(20): 3531-3534
DOI: 10.1055/s-2005-918489
DOI: 10.1055/s-2005-918489
PAPER
© Georg Thieme Verlag Stuttgart · New York
First Synthesis of N-Indigoglycosides - Analogues of Cancerostatic Akashines
Further Information
Received
9 October 2005
Publication Date:
24 November 2005 (online)
Publication History
Publication Date:
24 November 2005 (online)
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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