Multisite Modification of Neomycin B: Combined Mitsunobu and Click Chemistry Approach

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Title Multisite Modification of Neomycin B: Combined Mitsunobu and Click Chemistry Approach
Author Quader, Sabina; Boyd, Sue Elizabeth; Jenkins, Ian Douglas; Houston, Todd Ashley
Journal Name Journal of Organic Chemistry
Year Published 2007
Place of publication United States
Publisher The American Chemical Society
Abstract The aminoglycoside antibiotic neomycin B has been converted into several novel building blocks that can be used for the specific modification of three of the four ring systems. Under carefully controlled conditions, the Mitsunobu reaction can be used to selectively dehydrate the ido ring to give the talo epoxide, not a tricyclic aziridine-azetidine structure as has been claimed previously. Subsequently however, under more forcing conditions, the 2-deoxy streptamine ring undergoes Mitsunobu dehydration to give an aziridine. An unusual remote neighbouring group effect was observed. When the primary hydroxyl of the ribose ring was blocked, aziridine formation on the deoxystreptamine ring did not occur. Both the epoxide and epoxide-aziridine neomycin building blocks can be ring-opened with azide, and subjected to “click” type chemistry with terminal alkynes to generate a series of new neomycin analogues. These reactions can all be carried out without recourse to O-protecting groups. A detailed conformational analysis by NMR revealed some unexpected conformer preferences in these systems.
Peer Reviewed Yes
Published Yes
Publisher URI http://pubs.acs.org/journal/joceah
Alternative URI http://dx.doi.org/10.1021/jo0620967
Volume 72
Page from 1962
Page to 1979
ISSN 0022-3263
Date Accessioned 2008-02-29
Date Available 2009-12-02T05:54:38Z
Language en_AU
Research Centre Environmental Futures Research Institute; Eskitis Institute for Drug Discovery; Institute for Glycomics
Faculty Faculty of Science, Environment, Engineering and Technology
Subject PRE2009-Organic Chemical Synthesis
URI http://hdl.handle.net/10072/17941
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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