title: Stereochemistry of sagittamide A: prediction and confirmation.
abstract: [structure: see text] The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the 3JH,H profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed 1H NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Seike
authors.forename: Indranath
authors.initials: I
authors.lastname: Ghosh
authors.forename: Yoshito
authors.initials: Y
authors.lastname: Kishi
mesh_terms: D001688:Biological Products / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009952:Ornithine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D014633:Valine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D001688:Biological Products; C508005:sagittamide A; D009952:Ornithine; D014633:Valine