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dc.contributor.author
Sarotti, Ariel Marcelo
dc.date.available
2021-03-02T13:33:09Z
dc.date.issued
2020-09
dc.identifier.citation
Sarotti, 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; 11566-11570
dc.identifier.issn
0022-3263
dc.identifier.uri
http://hdl.handle.net/11336/127109
dc.description.abstract
The 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.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society
dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
DIPLOPYRONE
dc.subject
RELATIVE CONFIGURATION
dc.subject
ABSOLUTE CONFIGURATION
dc.subject
DP4+
dc.subject.classification
Química Orgánica
dc.subject.classification
Ciencias Químicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.title
In Silico Reassignment of (+)-Diplopyrone by NMR Calculations: Use of a DP4/ J-DP4/DP4+/DIP Tandem to Revise Both Relative and Absolute Configuration
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2021-02-10T21:08:26Z
dc.journal.volume
85
dc.journal.number
17
dc.journal.pagination
11566-11570
dc.journal.pais
Estados Unidos
dc.journal.ciudad
Washington D. C.
dc.description.fil
Fil: 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.journal.title
Journal of Organic Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://pubs.acs.org/doi/abs/10.1021/acs.joc.0c01563
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://doi.org/10.1021/acs.joc.0c01563
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