An attempt to determine the absolute configuration of two ascolactone stereoisomers with time-dependent density functional theory

Chirality
Simon F SeibertJörg Fleischhauer

Abstract

Two stereoisomers of ascolactone (A, B), natural products with two asymmetric carbon atoms, are isolated from the marine-derived fungus Ascochyta salicorniae. Although these compounds show virtually opposite CD spectra and [alpha]D, 1H- and 13C-NMR data exclude the presence of enantiomers and suggest ascolactone A and B to be epimeric lactones. By comparing the experimental CD spectra with those calculated employing time-dependent density functional theory (TDDFT), we elucidate the configuration at one of the asymmetric carbon atoms.

Citations

Jun 28, 2011·Analytical Chemistry·Victoria L BrewsterRoyston Goodacre
May 27, 2006·Organic & Biomolecular Chemistry·Simon F SeibertGabriele M König
Jan 14, 2011·Natural Product Reports·Mostafa E Rateb, Rainer Ebel
Dec 14, 2011·The Journal of Organic Chemistry·Kathrin H HopmannKenneth Ruud
Jun 13, 2014·The Journal of Physical Chemistry. a·Masamitsu WakabayashiShinichiro Nakamura

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