Atropoisomerism in Biflavones: The Absolute Configuration of (−)-Agathisflavone via Chiroptical Spectroscopy

The first natural occurrence in optically active form of the dimeric flavonoid agathisflavone and definition of its axial chirality using chiroptical spectroscopic methods are described. The experimental electronic circular dichroism, electronic dissymmetry factor, optical rotatory dispersion, vibra...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2016-10, Vol.79 (10), p.2530-2537
Main Authors: Covington, Cody L, Junior, Fernando M. S, Silva, Jessica H. S, Kuster, Ricardo M, de Amorim, Mauro B, Polavarapu, Prasad L
Format: Article
Language:English
Subjects:
Biflavonoids - chemistry
Circular Dichroism
Molecular Conformation
Molecular Structure
Optical Rotatory Dispersion
Stereoisomerism
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Summary:The first natural occurrence in optically active form of the dimeric flavonoid agathisflavone and definition of its axial chirality using chiroptical spectroscopic methods are described. The experimental electronic circular dichroism, electronic dissymmetry factor, optical rotatory dispersion, vibrational circular dichroism (VCD), and vibrational dissymmetry factor spectra of agathisflavone are presented and analyzed with their corresponding quantum chemical predictions to definitively assign the axial chirality of (−)-agathisflavone as (aS).
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.6b00395