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dc.contributor.authorJenkins, Ian D
dc.contributor.authorLacrampe, Fabienne
dc.contributor.authorRipper, Justin
dc.contributor.authorAlcaraz, Lilian
dc.contributor.authorVan Le, Phuc
dc.contributor.authorNikolakopoulos, George
dc.contributor.authorLeone, Priscila de Almeida
dc.contributor.authorWhite, Rodney H
dc.contributor.authorQuinn, Ronald J
dc.date.accessioned2017-05-03T11:15:19Z
dc.date.available2017-05-03T11:15:19Z
dc.date.issued2009
dc.date.modified2010-06-16T05:42:45Z
dc.identifier.issn0022-3263
dc.identifier.doi10.1021/jo802456w
dc.identifier.urihttp://hdl.handle.net/10072/30550
dc.description.abstractInspired by the novel spiro structures of a number of bioactive natural products such as the histrionicotoxins, a series of novel spiro scaffolds have been designed and robust syntheses developed. The scaffolds are ready-to-use building blocks and can be easily prepared on a 5-20 g scale. They contain two amino groups (one Boc-protected) and have been designed for ease of conversion to a lead generation library, using either amide formation or reductive amination procedures. The synthesis of the 1,9-diazaspiro[5.5]undecane and 3,7-diazaspiro[5.6]dodecane ring systems was achieved using RCM as the key step. A simple workup procedure is reported for the removal of highly colored ruthenium residues. The synthesis of the 1,8-diazaspiro[4.5]decane scaffold has been achieved using a bromine-mediated 5-endo cyclization of the corresponding 4-aminobutene intermediate under acidic conditions. This is the ?rst example of this type of cyclization to be reported. A novel mechanism involving a bromine transfer reaction from an initially formed bromonium ion to a neighboring nitrogen atom is suggested as the reason for the failure of this type of reaction under "normal" bromination conditions. An unusual rearrangement of a 1-acyl-1,9-diazaspiro[5.5]undecane to the corresponding 9-acyl-1,9-diazaspiro[5.5]undecane is reported.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoen_AU
dc.publisherAmerican Chemical Society
dc.publisher.placeUSA
dc.publisher.urihttp://pubs.acs.org/
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom1304
dc.relation.ispartofpageto1313
dc.relation.ispartofissue3
dc.relation.ispartofjournalJournal of Organic Chemistry
dc.relation.ispartofvolume74
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and Biomolecular Chemistry
dc.subject.fieldofresearchOrganic Chemistry
dc.subject.fieldofresearchcode0304
dc.subject.fieldofresearchcode0305
dc.titleSynthesis of Four Novel Natural Product Inspired Scaffolds for Drug Discovery
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.rights.copyright© 2009 American Chemical Society. Self-archiving of the author-manuscript version is not yet supported by this publisher. Please refer to the journal link for access to the definitive, published version or contact the authors for more information.
gro.date.issued2009
gro.hasfulltextNo Full Text
gro.griffith.authorJenkins, Ian D.
gro.griffith.authorQuinn, Ronald J.
gro.griffith.authorWhite, Rodney H.
gro.griffith.authorRipper, Justin A.
gro.griffith.authorLe, Van
gro.griffith.authorDe Almeida Leone, Priscila
gro.griffith.authorNikolakopoulos, George
gro.griffith.authorLacrampe, Fabienne


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