title: Structure Determination and Mechanism of Formation of a seco-Moreliane Derivative Supported by Computational Analysis.
abstract: Basic hydrolysis of a dichloromethane extract of Stevia lucida yielded (4R,5S,7R,9R,10R,11R)-7,9-dihydroxylongipin-2-en-1-one (1), which was oxidized and subjected to acidic conditions to generate the new seco-moreliane derivative 3. The structure of 3 was established based on NMR data interpretation and confirmed computationally. A plausible mechanism for the carbocationic rearrangement of the trione 2 to the seco-moreliane 3 was supported by DFT computations.
authors.affiliation: Laboratory of Natural Products, Department of Chemistry, Faculty of Sciences, University of "Los Andes" , Mérida 5101, Venezuela.
authors.forename: Pablo A
authors.identifier: 0000-0003-4456-3342
authors.initials: PA
authors.lastname: Chacón Morales
authors.affiliation: Laboratory of Natural Products, Department of Chemistry, Faculty of Sciences, University of "Los Andes" , Mérida 5101, Venezuela.
authors.forename: Juan M
authors.initials: JM
authors.lastname: Amaro-Luis
authors.affiliation: Department of Chemistry and Biochemistry, University of Denver , Denver, Colorado 80208, United States.
authors.forename: Andrei G
authors.identifier: 0000-0003-3066-517X
authors.initials: AG
authors.lastname: Kutateladze
mesh_terms: D006868:Hydrolysis; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D036625:Stevia / Q000737:chemistry*; D014687:Venezuela
chemical_list: D012717:Sesquiterpenes