Absolute configuration of curdione and its three
isomers by NMR, ECD and DFT calculations: an insight
into the scope of unsaturated ketone helicity rule
based on an ECD study

Absolute configuration of curdione and its three isomers by NMR, ECD and DFT calculations: an insight into the scope of unsaturated ketone helicity rule based on an ECD study

Feiting Zhang, Yuxin Li, Tianhui Zhu, Wenhe Zhang, Bin Qin*, Song You*

School of Life Sciences & Biopharmaceutical Sciences, Shenyang Pharmaceutical University, Shenyang 110016, China

Received:2016-06-30 Revised:2017-09-11 Online:2018-02-20 Published:2018-04-03
Contact: School of Life Sciences & Biopharmaceutical Sciences, Shenyang Pharmaceutical University, Shenyang ??00?6, China; E-mail: to- qinbin@?63.com (B. Qin); yousong206@aliyun.com (S. You); Tel.:+86-24-23986436.

Abstract

Abstract: The stereostructures of curdione and its other three isomers with two stereogenic centers, C-4 and C-7, were studied each by electronic circular dichroism (ECD) spectroscopy and nuclear magnetic resonance (NMR) spectroscopy for determination of their absolute configurations. Their expected spectra based upon the density functional theory calculations were reasonably well agreed on experimental spectra. Furthermore, it was reported for the first time that these compounds, which have the unsaturated ketone groups with the distance between the two unsaturated carbon atoms less than about 2.55Å, can be applied to the unsaturated ketone helicity rule.

Key words: Curdione, NMR, ECD, DFT, Helicity rul

Feiting Zhang, Yuxin Li, Tianhui Zhu, Wenhe Zhang, Bin Qin, Song You. Absolute configuration of curdione and its three isomers by NMR, ECD and DFT calculations: an insight into the scope of unsaturated ketone helicity rule based on an ECD study[J]. Asina Journal Of Traditional Medicines.

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