title: Predicting NMR spectra by computational methods: structure revision of hexacyclinol.
abstract: [structure: see text] The structure of the natural product hexacyclinol was reassigned from endoperoxide 1 to the diepoxide 7 on the basis of calculated (13)C chemical shift data using HF/3-21G geometries and mPW1PW91/6-31G(d,p) GIAO NMR predictions. These predictions correlate very well with experimental data for three other highly oxygenated natural products, elisapterosin B, maoecrystal V, and elisabethin A. Hexacyclinol is proposed to arise from acid-catalyzed rearrangement of panepophenanthrin in the presence of methanol.
authors.affiliation: Department of Chemistry, 1102 Natural Sciences II, University of California-Irvine, 92697-2025, USA. srychnov@uci.edu
authors.forename: Scott D
authors.initials: SD
authors.lastname: Rychnovsky
mesh_terms: D001688:Biological Products / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011083:Polycyclic Compounds / Q000737:chemistry*
chemical_list: D001688:Biological Products; D004852:Epoxy Compounds; D011083:Polycyclic Compounds; C469535:hexacyclinol