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Synthesis and structural elucidation of a phthalide analog using NMR analysis and DFT calculations

2019; Wiley; Volume: 58; Issue: 6 Linguagem: Inglês

10.1002/mrc.4976

1097-458X

Bryan Nickson Santana Pinto, Milena Galdino Teixeira, Elson S. Alvarenga,

Molecular spectroscopy and chirality

Abstract Phtalides are secondary metabolites found in several fungi with a wide range of biological activities. A novel phthalide analog was synthesized by Diels–Alder reaction between cyclopentadiene and 3,4‐dichlorofuran‐2(5 H )‐one. Quantum mechanical calculations were used in conjunction with the spectrometric methods to determine the structure of the title compound. The calculated NMR chemical shifts for eight candidate pairs of enantiomers were compared with the experimental NMR chemical shifts applying the DP4 probability and mean absolute errors methodology. DP4 analysis using 1 H and 13 C NMR chemical shifts without assignment of the signals presented 100% probability for the correct candidate structure 3d , proving the consistency of the method even without spectra interpretation. Results from theoretical calculation and NMR spectra interpretation were in agreement to the structure of rac ‐(3a R ,4 S ,4a S ,5 R ,8 S ,8a R ,9 R ,9a S )‐3a,9a‐dichloro‐3a,4,4a,5,8,8a,9,9a‐octahydro‐4,9:5,8‐dimethanonaphtho[2,3‐ c ]furan‐1(3 H )‐one.