Determination of absolute configuration using vibrational circular dichroism spectroscopy: phenyl glycidic acid derivatives obtained via asymmetric epoxidation using oxone and a keto bile acid

2005 ◽  
Vol 16 (15) ◽  
pp. 2653-2663 ◽  
Author(s):  
Frank J. Devlin ◽  
Philip J. Stephens ◽  
Olga Bortolini
Keyword(s):  
Circular Dichroism ◽  
Bile Acid ◽  
Absolute Configuration ◽  
Circular Dichroism Spectroscopy ◽  
Vibrational Circular Dichroism ◽  
Asymmetric Epoxidation ◽  
Determination Of Absolute Configuration ◽  
Circular Dichroïsm

scholarly journals Vibrational Circular Dichroism: A New Tool for the Solution-State Determination of the Structure and Absolute Configuration of Chiral Natural Product Molecules

2008 ◽  
Vol 3 (3) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Laurence A. Nafie
Keyword(s):  
Circular Dichroism ◽  
Natural Product ◽  
Absolute Configuration ◽  
Vibrational Circular Dichroism ◽  
Chiral Molecules ◽  
Solution State ◽  
X Ray Crystallography ◽  
Determination Of Absolute Configuration ◽  
Circular Dichroïsm

Vibrational circular dichroism (VCD) has been used in recent years to determine the absolute configuration of a number of natural product chiral molecules. In this brief review, these applications will be described and the methodology of VCD determination of absolute configuration (AC) will be explained. The principal advantages of VCD versus X-ray crystallography for absolute configuration determination are: 1) only solution-state samples are needed and therefore single crystals are not required, 2) high enantiomeric sample purity is not required, 3) high chemical purity is not required as long as impurities are not chiral and 4) solution-state conformations are obtained as an extra feature of the AC determination.

scholarly journals VCD Determination of the Absolute Configuration of Stypotriol

2009 ◽  
Vol 4 (8) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Marcelo A. Muñoz ◽  
Carlos Areche ◽  
Aurelio San-Martín ◽  
Juana Rovirosa ◽  
Pedro Joseph-Nathan
Keyword(s):  
Circular Dichroism ◽  
Natural Product ◽  
Absolute Configuration ◽  
Circular Dichroism Spectroscopy ◽  
Vibrational Circular Dichroism ◽  
Stypopodium Zonale ◽  
The Absolute ◽  
Circular Dichroïsm

The absolute configuration of the pentacyclic ichthyotoxin stypotriol, a constituent of Stypopodium zonale, was deduced to be 3S,5R,8R,9R,10S,13S,14S-(-)-1 by vibrational circular dichroism spectroscopy of the derived triacetate 2 in comparison to DFT B3LYP/DGDZVP calculations. Compound 2, C33H46O7 having 300 electrons, is the largest natural product successfully studied by VCD to date.

Sign in / Sign up

Export Citation Format

Share Document