Biomimetic synthesis of xuxuarines E alpha and E beta: Structure revision of Rzedowskia bistriterpenoids

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dc.contributor.authorJacobsen, Neil E.
dc.contributor.authorWijeratne, E. M. Kithsiri
dc.contributor.authorCorsino, Joaquim [UNESP]
dc.contributor.authorFurlan, Maysa [UNESP]
dc.contributor.authorBolzani, Vanderlan da Silva [UNESP]
dc.contributor.authorGunatilaka, A. A. Leslie
dc.contributor.institutionUniversity of Arizona
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.date.accessioned2014-05-20T14:20:17Z
dc.date.available2014-05-20T14:20:17Z
dc.date.issued2008-02-15
dc.description.abstractReaction of pristimerin with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) resulted in a biomimetic-type coupling leading to xuxuarines E alpha and E beta and not the previously reported Rzedowskia bistriterpenoids I and II suggesting that the structures proposed for these natural products need revision. A product obtained in this reaction by an unusual Diels-Alder addition followed by retro-Diels-Alder-type elimination was characterized as pristimerin dicyanophenalenedione. Complete H-1, and C-13 NMR spectral assignments of xuxuarines Ea and Eb have been made by the application of 1D and 2D NMR techniques. (c) 2007 Elsevier Ltd. All rights reserved.en
dc.description.affiliationUniv Arizona, Coll Agr & Life Sci, Off Arid Lands Studies, SW Ctr Nat Prod Res & Commercializat, Tucson, AZ 85706 USA
dc.description.affiliationUniv Arizona, Dept Chem, Coll Arts & Sci, Tucson, AZ 85721 USA
dc.description.affiliationUniv Estadual Paulista, Inst Quim, BR-14800900 Araraquara, SP, Brazil
dc.description.affiliationUnespUniv Estadual Paulista, Inst Quim, BR-14800900 Araraquara, SP, Brazil
dc.format.extent1884-1889
dc.identifierhttp://dx.doi.org/10.1016/j.bmc.2007.11.008
dc.identifier.citationBioorganic & Medicinal Chemistry. Oxford: Pergamon-Elsevier B.V. Ltd, v. 16, n. 4, p. 1884-1889, 2008.
dc.identifier.doi10.1016/j.bmc.2007.11.008
dc.identifier.issn0968-0896
dc.identifier.lattes1308042794786872
dc.identifier.lattes4484083685251673
dc.identifier.urihttp://hdl.handle.net/11449/26095
dc.identifier.wosWOS:000254080900027
dc.language.isoeng
dc.publisherPergamon-Elsevier B.V. Ltd
dc.relation.ispartofBioorganic & Medicinal Chemistry
dc.relation.ispartofjcr2.881
dc.relation.ispartofsjr0,871
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.titleBiomimetic synthesis of xuxuarines E alpha and E beta: Structure revision of Rzedowskia bistriterpenoidsen
dc.typeArtigo
dcterms.licensehttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dcterms.rightsHolderPergamon-Elsevier B.V. Ltd
unesp.author.lattes1308042794786872
unesp.author.lattes4484083685251673
unesp.campusUniversidade Estadual Paulista (Unesp), Instituto de Química, Araraquarapt

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