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Stereochemical Investigation of Macrocyclic Bisbibenzyls with a Stereogenic Center at One of the Ethylene Bridges

  作者 Xie, CF; Zhu, RX; Qu, JB; Wang, LN; Guo, DX; Yu, WT; Liu, CB; Lou, HX  
  选自 期刊  Helvetica Chimica Acta;  卷期  2011年94-11;  页码  2077-2086  
  关联知识点  
 

[摘要]7'-Hydroxyriccardin C (1) and marchantin E (2), two macrocyclic bisbibenzyls with a stereogenic center at the ethylene bridge from Chinese liverworts, were investigated stereochemically. Compound 1 was found to be optically active and occurred as a pair of dynamically interchangeable atropisomers at room temperature due to the low barrier of rotation around the biaryl bond, while 2 was a racemic mixture, which was successfully resolved by chiral HPLC into two enantiomers. Their absolute configurations were unequivocally assigned by analysis of temperature-dependent NMR spectra, X-ray crystallographic diffraction, and comparison of experimental and calculated ECD data.

 
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