Stereochemistry of sagittamide A: prediction and confirmation.
[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.
Seike
Hirofumi
H
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Ghosh
Indranath
I
Kishi
Yoshito
Y
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
D001688:Biological Products; C508005:sagittamide A; D009952:Ornithine; D014633:Valine