Absolute Configuration of a Rare Sesquiterpene: (+)-3-Ishwarone.

Junior FM, Covington CL, de Amorim MB, Velozo LS, Kaplan MA, Polavarapu PL
J Nat Prod. 2014 77 (8): 1881-6

PMID: 25051336 · DOI:10.1021/np500363e

To determine the absolute configuration of 3-ishwarone, the experimental electronic circular dichroism (ECD), electronic dissymmetry factor (EDF), optical rotatory dispersion (ORD), vibrational circular dichroism (VCD), and vibrational dissymmetry factor (VDF) spectra of (+)-3-ishwarone are analyzed with the corresponding density functional theoretical predictions for different diastereomers. ECD and ORD spectra by themselves could not facilitate the determination of the absolute configuration of this molecule. However, the magnitude of the experimental EDF of (+)-3-ishwarone is found to match better with that predicted for the (1R,2S,4S,5R,9R,11R) diastereomer. The analyses of similarity measures between experimental and predicted spectra for VCD and VDF clearly suggested that the absolute configuration of (+)-3-ishwarone is (1R,2S,4S,5R,9R,11R).

MeSH Terms (9)

Algorithms Brazil Circular Dichroism Molecular Structure Optical Rotatory Dispersion Peperomia Plant Components, Aerial Sesquiterpenes Stereoisomerism

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