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dc.contributor.authorLoughlin, Wendy A
dc.contributor.authorSchweiker, Stephanie S
dc.contributor.authorJenkins, Ian D
dc.contributor.authorHenderson, Luke C
dc.date.accessioned2017-05-03T12:22:37Z
dc.date.available2017-05-03T12:22:37Z
dc.date.issued2013
dc.date.modified2014-06-11T03:12:16Z
dc.identifier.issn0040-4020
dc.identifier.doi10.1016/j.tet.2012.12.004
dc.identifier.urihttp://hdl.handle.net/10072/52568
dc.description.abstractAn effective synthesis of 4.5-spiro lactams 28/29, has been completed in nine steps with an overall yield of 5.8%. The 4.5-spiro lactams were made from 2-allyl-Cbz-Pro-OMe 21, which was converted into the corresponding alcohol 22 via a hindered borane reaction with (2-methylbutyl)2borane. Subsequent Swern oxidation of 22 gave novel aldehyde 23. Aldehyde 23 was treated under Bucherer-Bergs reaction conditions to give hydantoin 26, which was opened to the corresponding amino acid 30 using di-tert-butyl dicarbonate and DMAP followed by hydrolysis. Treatment of amino acid 30 with acidic methanol gave 4.5-spiro lactams 28/29. Only 4.5-spiro lactam 29 displayed moderate activity against GPa with an IC50 of 241 卮
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.format.extent352350 bytes
dc.format.mimetypeapplication/pdf
dc.languageEnglish
dc.language.isoeng
dc.publisherElsevier
dc.publisher.placeUnited Kingdom
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom1576
dc.relation.ispartofpageto1582
dc.relation.ispartofissue5
dc.relation.ispartofjournalTetrahedron
dc.relation.ispartofvolume69
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchMedicinal and biomolecular chemistry not elsewhere classified
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchOrganic chemical synthesis
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode340499
dc.subject.fieldofresearchcode3405
dc.subject.fieldofresearchcode340503
dc.titleSynthesis and evaluation of C8-substituted 4.5-spiro lactams as Glycogen Phosphorylase a inhibitors
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.rights.copyright© 2013 Elsevier. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version.
gro.date.issued2013
gro.hasfulltextFull Text
gro.griffith.authorJenkins, Ian D.
gro.griffith.authorLoughlin, Wendy A.


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