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

Covington CL, Junior FM, Silva JH, Kuster RM, de Amorim MB, Polavarapu PL
J Nat Prod. 2016 79 (10): 2530-2537

PMID: 27723329 · DOI:10.1021/acs.jnatprod.6b00395

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).

MeSH Terms (6)

Biflavonoids Circular Dichroism Molecular Conformation Molecular Structure Optical Rotatory Dispersion Stereoisomerism

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