Revising the absolute configurations of coatlines via density functional theory calculations of electronic circular dichroism spectra

Coatline A () and α-epi-coatline A () co-occur in the trunk extract of Andira coriacea. Inspection of their chiroptical properties led to intriguing results. After a careful examination of the experimental data used for the previously reported absolute configuration of these compounds, some uncertainties were identified. A combined theoretical approach including conformational analyses and calculation of electronic circular dichroism (ECD) spectra, in addition with experimental data obtained for schoepfin A () and the new schoepfin D () isolated from Senna quinquangulata, allowed the revision of the absolute configuration of coatlines A () and B (). Chirality 25:180-184, 2013. © 2012 Wiley Periodicals, Inc.