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dc.contributor.authorQuader, Sabinaen_US
dc.contributor.authorBoyd, Sueen_US
dc.contributor.authorJenkins, Ianen_US
dc.contributor.authorHouston, Todden_US
dc.date.accessioned2017-04-24T07:58:26Z
dc.date.available2017-04-24T07:58:26Z
dc.date.issued2007en_US
dc.date.modified2009-12-02T05:54:38Z
dc.identifier.issn00223263en_US
dc.identifier.doi10.1021/jo0620967en_AU
dc.identifier.urihttp://hdl.handle.net/10072/17941
dc.description.abstractThe 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.en_US
dc.description.peerreviewedYesen_US
dc.description.publicationstatusYesen_AU
dc.languageEnglishen_US
dc.language.isoen_AU
dc.publisherThe American Chemical Societyen_US
dc.publisher.placeUnited Statesen_US
dc.publisher.urihttp://pubs.acs.org/journal/joceahen_AU
dc.relation.ispartofstudentpublicationNen_AU
dc.relation.ispartofpagefrom1962en_US
dc.relation.ispartofpageto1979en_US
dc.relation.ispartofjournalJournal of Organic Chemistryen_US
dc.relation.ispartofvolume72en_US
dc.rights.retentionYen_AU
dc.subject.fieldofresearchcode250301en_US
dc.titleMultisite Modification of Neomycin B: Combined Mitsunobu and Click Chemistry Approachen_US
dc.typeJournal articleen_US
dc.type.descriptionC1 - Peer Reviewed (HERDC)en_US
dc.type.codeC - Journal Articlesen_US
gro.facultyAn Unassigned Group, An Unassigned Departmenten_US
gro.date.issued2007
gro.hasfulltextNo Full Text


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