The application of empirical methods of (13)C NMR chemical shift prediction as a filter for determining possible relative stereochemistry.
The reliable determination of stereocenters contained within chemical structures usually requires utilization of NMR data, chemical derivatization, molecular modeling, quantum-mechanical (QM) calculations and, if available, X-ray analysis. In this article, we show that the number of stereoisomers which need to be thoroughly verified, can be significantly reduced by the application of NMR chemical shift calculation to the full stereoisomer set of possibilities using a fragmental approach based on HOSE codes. The applicability of this suggested method is illustrated using experimental data published for a series of complex chemical structures.
Elyashberg
Mikhail E
ME
Advanced Chemistry Development, Moscow Department, 6 Akademik Bakulev Street, Moscow 117513, Russian Federation.
Blinov
Kirill A
KA
Williams
Antony J
AJ
D000470:Alkaloids / Q000737:chemistry; D002247:Carbon Isotopes; D003198:Computer Simulation; D016208:Databases, Factual; D004224:Diterpenes / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods* / Q000592:standards*; D008956:Models, Chemical; D008968:Molecular Conformation; D012015:Reference Standards; D012717:Sesquiterpenes / Q000737:chemistry; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry; D013729:Terpenes / Q000737:chemistry
D000470:Alkaloids; D002247:Carbon Isotopes; D004224:Diterpenes; D012717:Sesquiterpenes; D013256:Steroids; D013729:Terpenes; C521923:artarborol