Chiroptical studies on brevianamide B: vibrational and electronic circular dichroism confronted

The Journal of Organic Chemistry
Patrick BultinckMarko Weimar

Abstract

Chiroptical spectroscopies, such as electronic circular dichroism (ECD) and vibrational circular dichroism (VCD), are highly sensitive techniques to probe molecular conformation, configuration, solvation, and aggregation. Here we report the application of these techniques to study the fungal metabolite brevianamide B. Comparison of the experimental ECD and VCD spectra with the density functional theory simulated counterparts establishes that VCD is the more reliable technique to assign absolute configuration due to the larger functional and dispersion dependence of computed ECD spectra. Despite a low amount of available material and a relatively unusual example of using VCD carbonyl multiplets, the absolute configuration could be reliably predicted, strengthening the case for application of VCD in the study of complex natural products. Spectral and crystallographic evidence for or against the formation of a dimeric aggregate is discussed; in solution, the VCD spectra strongly suggest only monomeric species are present.

References

May 31, 2002·Acta Crystallographica. Section B, Structural Science·Frank H Allen
Feb 19, 2003·Accounts of Chemical Research·Robert M Williams, Rhona J Cox
Aug 25, 2006·The Journal of Physical Chemistry. a·Tom KuppensPatrick Bultinck
Nov 19, 2008·Physical Chemistry Chemical Physics : PCCP·Guochun Yang, Yunjie Xu
Apr 22, 2009·Accounts of Chemical Research·Parag MukhopadhyayDavid N Beratan
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Jan 7, 2014·Natural Product Reports·John W BluntMichèle R Prinsep

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Citations

Jul 2, 2020·Natural Product Reports·Prasad L Polavarapu, Ernesto Santoro
Feb 23, 2020·Chirality·František KrálíkVladimír Setnička
Nov 5, 2021·Nature Communications·Qiuhong ChengPengyao Xing

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