title: Stereostructure reassignment and absolute configuration of isoepitaondiol, a meroditerpenoid from Stypopodium flabelliforme.
abstract: Careful examination of the published NMR data for isoepitaondiol, a meroditerpenoid from Stypopodium flabelliforme, suggests that its published structure 1 must be revised. On the basis of extensive 1D and 2D NMR studies, we now propose that structure 2, with a trans-anti-trans-anti-cis arrangement fits isoepitaondiol diacetate. The relative configuration of 2 was confirmed by single-crystal X-ray diffraction, while the absolute configuration was evidenced by vibrational circular dichroism in combination with DFT B3LYP/DGDZVP calculations.
authors.affiliation: Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile.
authors.forename: Carlos
authors.initials: C
authors.lastname: Areche
authors.forename: Aurelio
authors.initials: A
authors.lastname: San-Martín
authors.forename: Juana
authors.initials: J
authors.lastname: Rovirosa
authors.forename: Marcelo A
authors.initials: MA
authors.lastname: Muñoz
authors.forename: Angelina
authors.initials: A
authors.lastname: Hernández-Barragán
authors.forename: Maria A
authors.initials: MA
authors.lastname: Bucio
authors.forename: Pedro
authors.initials: P
authors.lastname: Joseph-Nathan
mesh_terms: D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification*; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D004224:Diterpenes; C546848:isoepitaondiol