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Assignment of Configuration in a Series of Dioxolanone‐Type Secondary Metabolites from Guignardia bidwellii – A Comparison of VCD and ECD Spectroscopy
Author(s) -
Andernach Lars,
Sandjo Louis P.,
Liermann Johannes C.,
Buckel Iris,
Thines Eckhard,
Opatz Till
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300530
Subject(s) - vibrational circular dichroism , circular dichroism , chemistry , spectroscopy , absolute configuration , time dependent density functional theory , density functional theory , computational chemistry , stereochemistry , physics , quantum mechanics
The absolute configurations of a series of phytotoxic dioxolanone‐type secondary metabolites isolated from culture filtrates of the grape black rot fungus Guignardia bidwellii were determined by vibrational circular dichroism (VCD) spectroscopy in the mid‐IR frequency range. Comparison of the recorded data with DFT calculations showed good agreement between experiment and theory for VCD, whereas electronic circular dichroism (ECD) data for the compounds matched poorly with the predicted spectra obtained by time‐dependent DFT (TDDFT) calculations at the same level of theory.