title: Strength by joining methods: combining synthesis with NMR, IR, and vibrational circular dichroism spectroscopy for the determination of the relative configuration in hemicalide.
abstract: The relative configuration of a key subunit of hemicalide, a recently isolated, highly bioactive marine natural product having potent antiproliferative activity against a panel of human cancer cell lines, was assigned by combining stereocontrolled synthesis of model substrates with NMR, IR, and vibrational circular dichroism (VCD) spectroscopy. The assignment of the absolute configuration of asymmetric carbon center C42 in two structurally complex epimeric substructures containing six stereocenters by VCD analysis illustrates the power and reliability of combining methods.
authors.affiliation: Department of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281-S3, 9000 Ghent (Belgium); Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp (Belgium).
authors.forename: Ewoud
authors.initials: E
authors.lastname: De Gussem
authors.forename: Wouter
authors.initials: W
authors.lastname: Herrebout
authors.forename: Simon
authors.initials: S
authors.lastname: Specklin
authors.forename: Christophe
authors.initials: C
authors.lastname: Meyer
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
authors.forename: Patrick
authors.initials: P
authors.lastname: Bultinck
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002942:Circular Dichroism / Q000379:methods*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D013055:Spectrophotometry, Infrared / Q000379:methods; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D061065:Polyketides; C586602:hemicalide
keywords: NMR spectroscopy; circular dichroism; configuration determination; natural products; structure elucidation