In Silico Reassignment of (+)-Diplopyrone by NMR Calculations: Use of a DP4/ J-DP4/DP4+/DIP Tandem to Revise Both Relative and Absolute Configuration

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dc.conicet.fuenteindividual
dc.conicet.organizacionConsejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario
dc.conicet.paisOrganizacionArgentina
dc.conicet.produccionid9023316
dc.contributor.authorSarotti, Ariel Marcelo
dc.date.accessioned2021-03-02T13:33:09Z
dc.date.available2021-03-02T13:33:09Z
dc.date.issued2020-09
dc.date.updated2021-02-10T21:08:26Z
dc.description.abstractThe structural revision of natural (+)-diplopyrone (ND) was achieved by quantum NMR calculations. A DP4/J-DP4/DP4+ tandem suggested 3 as the most likely structure, but ECD calculations did not match the experimental values. The second more probable structure (6epi-1) showed the right ECD spectrum and high DP4/DP4+ probabilities obtained after fitting. However, further analysis of the MTPA-ND derivatives by DP4+/DIP calculations demonstrated that the absolute configuration at C-9 had been incorrectly assigned. Then, the structure of ND was proposed as ent-3.es
dc.description.filFil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
dc.formatapplication/pdfes
dc.identifier.citationSarotti, Ariel Marcelo; In Silico Reassignment of (+)-Diplopyrone by NMR Calculations: Use of a DP4/ J-DP4/DP4+/DIP Tandem to Revise Both Relative and Absolute Configuration; American Chemical Society; Journal of Organic Chemistry; 85; 17; 9-2020; 11566-11570es
dc.identifier.institucionalCONICET
dc.identifier.issn0022-3263es
dc.identifier.repoCONICET Digital
dc.identifier.urihttp://hdl.handle.net/11336/127109
dc.journal.ciudadWashington D. C.es
dc.journal.number17es
dc.journal.pagination11566-11570es
dc.journal.paisEstados Unidoses
dc.journal.titleJournal of Organic Chemistryes
dc.journal.volume85es
dc.language.isoenges
dc.publisherAmerican Chemical Societyes
dc.relation.alternativeidinfo:eu-repo/semantics/altIdentifier/doi/https://pubs.acs.org/doi/abs/10.1021/acs.joc.0c01563
dc.relation.alternativeidinfo:eu-repo/semantics/altIdentifier/doi/https://doi.org/10.1021/acs.joc.0c01563
dc.rightsinfo:eu-repo/semantics/restrictedAccess*
dc.rights.urihttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/*
dc.subjectDIPLOPYRONEes
dc.subjectRELATIVE CONFIGURATIONes
dc.subjectABSOLUTE CONFIGURATIONes
dc.subjectDP4+es
dc.subject.classificationQuímica Orgánicaes
dc.subject.classificationCiencias Químicases
dc.subject.classificationCIENCIAS NATURALES Y EXACTASes
dc.titleIn Silico Reassignment of (+)-Diplopyrone by NMR Calculations: Use of a DP4/ J-DP4/DP4+/DIP Tandem to Revise Both Relative and Absolute Configurationes
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:ar-repo/semantics/artículo
dc.typeinfo:eu-repo/semantics/publishedVersion

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