Pauson-Khand Adducts of N-Boc-propargylamine: A New Approach to 4,5-Disubstituted Cyclopentenones

dc.contributor.authorAiguabella Font, Núria
dc.contributor.authorPesquer, Albert
dc.contributor.authorVerdaguer i Espaulella, Xavier
dc.contributor.authorRiera i Escalé, Antoni
dc.date.accessioned2014-02-20T13:16:35Z
dc.date.available2014-05-28T22:02:23Z
dc.date.issued2013-05-28
dc.date.updated2014-02-20T12:18:26Z
dc.description.abstractA new approach to the synthesis of 4,5-disubstituted cyclopentenones is described. The strategy is based on the Pauson-Khand (PK) reaction of norbornadiene and N-Boc-propargylamine as alkyne with a masked leaving group, which can be eliminated at will. This approach to the synthesis of 4,5-disubstituted cyclopentenones overcomes the problem of using the alkylation to introduce the alpha-side-chain. As an example, prostane 13-epi-12-oxo-phytodienoic acid (13-epi-12-oxo-PDA) methyl ester was synthesized.
dc.format.extent4 p.
dc.format.mimetypeapplication/pdf
dc.identifier.idgrec632485
dc.identifier.issn1523-7060
dc.identifier.urihttps://hdl.handle.net/2445/50467
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.isformatofVersió postprint del document publicat a: http://dx.doi.org/10.1021/ol400999a
dc.relation.ispartofOrganic Letters, 2013, vol. 15, num. 11, p. 2696-2699
dc.relation.urihttp://dx.doi.org/10.1021/ol400999a
dc.rights(c) American Chemical Society , 2013
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.sourceArticles publicats en revistes (Química Inorgànica i Orgànica)
dc.subject.classificationCiclització (Química)
dc.subject.classificationQuímica biorgànica
dc.subject.classificationCompostos orgànics
dc.subject.classificationSíntesi orgànica
dc.subject.classificationHormones
dc.subject.classificationEfecte de l'estrès sobre les plantes
dc.subject.classificationEstrès (Psicologia)
dc.subject.classificationProstaglandines
dc.subject.classificationBiomolècules
dc.subject.otherRing formation (Chemistry)
dc.subject.otherBioorganic chemistry
dc.subject.otherOrganic compounds
dc.subject.otherOrganic synthesis
dc.subject.otherHormones
dc.subject.otherEffect of stress on plants
dc.subject.otherStress (Psychology)
dc.subject.otherProstaglandins
dc.subject.otherBiomolecules
dc.titlePauson-Khand Adducts of N-Boc-propargylamine: A New Approach to 4,5-Disubstituted Cyclopentenoneseng
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/acceptedVersion

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