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Determination of the absolute configurations of natural products via density functional theory calculations of vibrational circular dichroism, electronic circular dichroism, and optical rotation: The iso‐schizozygane alkaloids isoschizogaline and isoschizogamine
Author(s) -
Stephens Philip J.,
Pan JianJung,
Devlin Frank J.,
Urbanová Marie,
Julínek Ondřej,
Hájíček Josef
Publication year - 2008
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20466
Subject(s) - chemistry , circular dichroism , vibrational circular dichroism , optical rotation , density functional theory , rotation (mathematics) , specific rotation , time dependent density functional theory , molecular physics , computational chemistry , crystallography , stereochemistry , organic chemistry , geometry , mathematics
The development of density functional theory (DFT) methods for the calculation of vibrational circular dichroism (VCD), electronic circular dichroism (ECD), and transparent spectral region optical rotation (OR) has revolutionized the determination of the absolute configurations (ACs) of chiral molecules using these chiroptical properties. We report the concerted application of DFT calculations of VCD, ECD, and OR to the determination of the ACs of the isoschizozygane alkaloid natural products, isoschizogaline, and isochizogamine, whose ACs have not previously been determined. The ACs of naturally occurring (−)‐isoschizogaline and (−)‐isoschizogamine, are both determined definitively to be 2 R , 7 R , 20 S , 21 S . Chirality, 2008. © 2007 Wiley‐Liss, Inc.