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dc.contributor.authorRodríguez, Carmenes_ES
dc.contributor.authorMartín, Tomáses_ES
dc.contributor.authorMartín, Víctor S.es_ES
dc.date.accessioned2020-05-21T12:34:11Z-
dc.date.available2020-05-21T12:34:11Z-
dc.date.issued1996-11-29-
dc.identifier.citationJournal of Organic Chemistry 61(24): 8448–8452 (1996)es_ES
dc.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/10261/211873-
dc.description.abstractThe synthesis of isoavenaciolide and avenaciolide in their natural enantiomeric forms are described. In both syntheses, α-(phenylthio)-β-[(methoxycarbonyl)methyl]-γ-lactones obtained by the base-induced cyclization of enantiomerically enriched γ-[(phenylthio)acyl] α,β-unsaturated esters were used as starting materials. In the isoavenaciolide synthesis the key step is the stereoselective hydroxylation of the enolate generated in the (methoxycarbonyl)methyl chain that permits the bis-lactonization by a double transesterification. The configuration in the quaternary center vicinal to the carbonyl group in the ring was critical in order to obtain successfully the α-methylene lactone. In avenaciolide, the stereoselective synthesis of the bis-lactone unit was performed taking advantage of the presence of the phenyl sulfide group which by previous activation was used as leaving group to obtain the fused ring by an intramolecular substitution utilizing the carboxylate of the β-substituent as nucleophile. In this case, the α-methylene lactone was obtained by previously reported methodology.es_ES
dc.language.isoenges_ES
dc.publisherAmerican Chemical Societyes_ES
dc.relation.isversionofPostprintes_ES
dc.rightsclosedAccesses_ES
dc.subjectSulfideses_ES
dc.subjectLactoneses_ES
dc.subjectCarbonylses_ES
dc.subjectOrganic compoundses_ES
dc.subjectMolecular structurees_ES
dc.titleA New Stereoselective Synthesis of (−)-Isoavenaciolide and (−)-Avenaciolidees_ES
dc.typeartículoes_ES
dc.identifier.doi10.1021/jo9611935-
dc.description.peerreviewedPeer reviewedes_ES
dc.relation.publisherversionhttps://doi.org/10.1021/jo9611935es_ES
dc.identifier.e-issn1520-6904-
dc.rights.licensehttps://creativecommons.org/licenses/by/4.0/es_ES
dc.relation.csicNoes_ES
oprm.item.hasRevisionno ko 0 false*
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