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Stereochemical Investigation of Macrocyclic Bisbibenzyls with a Stereogenic Center at One of the Ethylene Bridges.
- Source :
- Helvetica Chimica Acta; Nov2011, Vol. 94 Issue 11, p2077-2086, 10p
- Publication Year :
- 2011
-
Abstract
- 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 0018019X
- Volume :
- 94
- Issue :
- 11
- Database :
- Complementary Index
- Journal :
- Helvetica Chimica Acta
- Publication Type :
- Academic Journal
- Accession number :
- 67195926
- Full Text :
- https://doi.org/10.1002/hlca.201100172