title: Determination of the absolute configuration of the natural product Klaivanolide via density functional calculations of vibrational circular dichroism (VCD).
abstract: The absolute configuration (AC) of the antiprotozoal lactone, Klaivanolide, 1, from Uvaria klaineana, has been determined using Vibrational Circular Dichroism (VCD) spectroscopy. The experimental VCD spectrum of the (+) enantiomer of 1 was measured. To analyze the AC of (+)-1, the conformationally-averaged VCD spectrum of 7-S-1 was calculated using density functional theory (DFT) and the GAUSSIAN 03 program. The B3PW91/TZ2P conformationally-averaged VCD spectrum of 7-S-1 proves that the AC of 1 is 7-S-(+).
authors.affiliation: Department of Chemistry, University of Southern California, Los Angeles, California 90089-0482, USA.
authors.forename: Frank J
authors.initials: FJ
authors.lastname: Devlin
authors.forename: Philip J
authors.initials: PJ
authors.lastname: Stephens
authors.forename: Bruno
authors.initials: B
authors.lastname: Figadère
mesh_terms: D001688:Biological Products / Q000737:chemistry*; D002942:Circular Dichroism / Q000379:methods*; D007783:Lactones / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D013816:Thermodynamics; D031046:Uvaria / Q000737:chemistry; D014732:Vibration
chemical_list: D001688:Biological Products; D007783:Lactones; C465329:klaivanolide