Application of Lanthanide Shift Reagent to the <sup>1</sup>H-NMR Assignments of Acridone Alkaloids

This study investigates the application of the paramagnetic shift reagent tris(dipivaloylmethanato)-europium(III) in NMR spectral studies of permethoxyacridone alkaloids (<b>1</b>–<b>3</b>) and pyranoacridone alkaloids (<b>4</b>–<b>6</b>). The induced...

Full description

Bibliographic Details
Main Authors: Sio-Hong Lam, Hsin-Yi Hung, Ping-Chung Kuo, Daih-Huang Kuo, Fu-An Chen, Tian-Shung Wu
Format: Article
Language:English
Published: MDPI AG 2020-11-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/25/22/5383
Description
Summary:This study investigates the application of the paramagnetic shift reagent tris(dipivaloylmethanato)-europium(III) in NMR spectral studies of permethoxyacridone alkaloids (<b>1</b>–<b>3</b>) and pyranoacridone alkaloids (<b>4</b>–<b>6</b>). The induced chemical shifts (∆δ) of all protons were observed for the same molecule, and were compared to deduce the positions resulting from the distance nearby the Eu(dpm)<sub>3</sub>. Assignment of the H-2, H-4 and H-8 of polysubstituted acridones could be distinguished based on the least-squares method of lanthanide-induced shifts plotted against the mole ratios of Eu(dpm)<sub>3</sub> to the substrate. The developed method is not only potentially useful for determining the planar structures of polysubstituted compounds, such as acridones, anthraquinones, xanthones, flavonoids, and phenanthrenes, but also applicable for their stereochemistry.
ISSN:1420-3049