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From Relative to Absolute Configuration of Complex Natural Products: Interplay Between NMR, ECD, VCD, and ORD Assisted by ab initio Calculations

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This minireview is addressed to readers with a background in basic organic chemistry and spectroscopy, but without a specific knowledge of NMR, ECD, VCD and ORD. Herein we summarize the role of quantum mechanical ab initio prediction of spectral properties in NMR and chiroptical spectroscopies. Illustrative examples of the application of prediction of chemical shifts and scalar couplings to the determination of chemical constitution and relative configurations of natural products are presented. Once the relative configuration is determined, the absolute configuration can be established with the help of ECD, VCD and ORD spectroscopies assisted by quantum mechanical prediction of the corresponding spectra. The scope, limitations and advantages of these chiroptical spectroscopies are presented, in order to help the reader in choosing a suitable combination of ab initio and spectroscopic tools when facing a particular problem.

Keywords: Chemical shielding; Chiroptical method; Diamagnetic (DSO) spin-orbit terms; ECD; Fermi-Contact term (FC); Hartree-Fock methods; Hierarchical organization of spherical environments (HOSE); IR-silent solvents; NMR; Non hybrid generalized gradient functionals (GGA); ORD; Optical rotation (OR); Paramagnetic (PSO); Potential energy surface (PES); Relative configuration determination; Spindipolar term (SD); VCD; X-ray crystal analysis; ab initio; absolute configuration determination; natural products; quantum mechanical (QM) modeling

Document Type: Research Article

Publication date: September 1, 2010

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