title: Stereostructure assignment of medium-sized rings through an NMR-computational combined approach. Application to the new germacranes ketopelenolides C and D.
abstract: The new germacrane derivatives ketopelenolides C and D have been isolated from great mugwort (Artemisia arborescens). Their stereostructure elucidation exemplifies some of the most common pitfalls facing the configurational assignment of medium-sized polyfunctionalized compounds. It was established through a combined strategy including chemical derivatization, NMR data analysis, molecular modeling, and quantum-mechanical calculations including a comparison between experimental 13C NMR data and a Boltzmann-weighted average of DFT-calculated 13C NMR chemical shifts.
authors.affiliation: Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli "Federico II", Via D. Montesano 49, 80131 Naples, Italy.
authors.forename: Ernesto
authors.initials: E
authors.lastname: Fattorusso
authors.forename: Paolo
authors.initials: P
authors.lastname: Luciano
authors.forename: Adriana
authors.initials: A
authors.lastname: Romano
authors.forename: Orazio
authors.initials: O
authors.lastname: Taglialatela-Scafati
authors.forename: Giovanni
authors.initials: G
authors.lastname: Appendino
authors.forename: Marianna
authors.initials: M
authors.lastname: Borriello
authors.forename: Caterina
authors.initials: C
authors.lastname: Fattorusso
mesh_terms: D019306:Artemisia / Q000737:chemistry*; D003198:Computer Simulation; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D045788:Sesquiterpenes, Germacrane / Q000737:chemistry* / Q000302:isolation & purification*; D013237:Stereoisomerism
chemical_list: D045788:Sesquiterpenes, Germacrane; C534382:ketopelenolide C; C534381:ketopelenolide D