title: Absolute Configuration of a Rare Sesquiterpene: (+)-3-Ishwarone.
abstract: 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).
authors: Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro , 21941-902, Rio de Janeiro, RJ, Brazil.
authors: Fernando M S
authors: FM
authors: Junior
authors: Department of Chemistry, Vanderbilt University , Nashville, Tennessee 37235, United States.
authors: Cody L
authors: CL
authors: Covington
authors: Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro , 21941-902, Rio de Janeiro, RJ, Brazil.
authors: Mauro B
authors: MB
authors: de Amorim
authors: Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro , 21941-902, Rio de Janeiro, RJ, Brazil.
authors: Leosvaldo S M
authors: LS
authors: Velozo
authors: Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro , 21941-902, Rio de Janeiro, RJ, Brazil.
authors: Maria A C
authors: MA
authors: Kaplan
authors: Department of Chemistry, Vanderbilt University , Nashville, Tennessee 37235, United States.
authors: Prasad L
authors: PL
authors: Polavarapu
mesh_terms: D000465:Algorithms; D001938:Brazil; D002942:Circular Dichroism; D015394:Molecular Structure; D009905:Optical Rotatory Dispersion; D036941:Peperomia / Q000737:chemistry; D035261:Plant Components, Aerial / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C000601981:3-ishwarone; D012717:Sesquiterpenes