Determination of the Absolute Configuration of Flexible Molecules by ab Initio ORD Calculations:  A Case Study with Cytoxazones and Isocytoxazones

Ab initio calculations of the optical rotatory power of the natural cytokine modulator cytoxazone 1 and its trans-diastereomer 2, as well as the structural isomers cis-3 and trans-4 isocytoxazones, have been performed at four different wavelengths (589, 546, 435, and 405 nm) by Density Functional Th...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-08, Vol.70 (17), p.6557-6563
Main Authors: Giorgio, Egidio, Roje, Marin, Tanaka, Katsunori, Hamersak, Zdenko, Sunjic, Vitomir, Nakanishi, Koji, Rosini, Carlo, Berova, Nina
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Oxazoles - chemistry
Preparations and properties
Spectrum Analysis
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Summary:Ab initio calculations of the optical rotatory power of the natural cytokine modulator cytoxazone 1 and its trans-diastereomer 2, as well as the structural isomers cis-3 and trans-4 isocytoxazones, have been performed at four different wavelengths (589, 546, 435, and 405 nm) by Density Functional Theory. The calculation of ORD curves provides a reliable method for the assignment of absolute configuration of these conformationally flexible molecules. The absolute configurations of isocytoxazones has been established as (+)-(4R,5S)-cis-3 and (+)-(4S,5S)-trans-4.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048023+