Progressive-convergent elucidation of stereochemistry in complex polyols. The absolute configuration of (-)-sagittamide A.
The absolute stereostructure of sagittamide A (1), a O-hexacetyl long-chain hexahydroxy-alpha,omega-dicarboxylic acid, was assigned using a progressive-convergent approach that integrates three powerful regimens for stereochemical analysis of acyclic natural products: J-based analysis, 13C NMR universal database comparisons, and exciton coupling circular dichroism.
Lievens
Sarah C
SC
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093, USA.
Molinski
Tadeusz F
TF
D002942:Circular Dichroism; D008968:Molecular Conformation; D019906:Nuclear Magnetic Resonance, Biomolecular; D009952:Ornithine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D014633:Valine / Q000031:analogs & derivatives* / Q000737:chemistry
C508005:sagittamide A; D009952:Ornithine; D014633:Valine