IQUIR 05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
In Silico Reassignment of (+)-Diplopyrone by NMR Calculations: Use of a DP4/J-DP4/DP4+/DIP Tandem to Revise Both Relative and Absolute Configuration
Autor/es:
SAROTTI, A.M.*
Revista:
JOURNAL OF ORGANIC CHEMISTRY
Editorial:
AMER CHEMICAL SOC
Referencias:
Lugar: Washington; Año: 2020 vol. 85 p. 11566 - 11570
ISSN:
0022-3263
Resumen:
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.
