Combined 13C NMR and DFT/GIAO studies of the polyketides Aurasperone A and Fonsecinone A

Abstract

Structural characterization by NMR spectroscopy and DFT calculations was performed for two dimeric naphtho-γ-pyrones, the polyketides Aurasperone A and Fonsecinone A. Experimental data (13C NMR chemical shifts and interatomic geometries) were found to be in reasonable agreement with theoretical ones, obtained at B3LYP level for three different basis sets (6-31G/6-31G(d)/6-31G(d,p)). Additionally, the dipolar moments calculation allowed explaining the different solubility for these molecules. The 13C NMR theoretical chemical shifts were calculated with the GIAO method and the solvent effects were taken into account by means of the PCM approximation. In this work, the DFT/GIAO methodology shows to be a reliable tool in the assignment of experimental NMR chemical shifts of similar molecules.