Publication Date:
2014-05-09
Description:
Methods were developed and optimized for the preparation of the 2,3- cis - and the 10,11- cis -isomers of silybin by the Lewis acid catalyzed (BF 3 ∙OEt 2 ) isomerization of silybins A ( 1a ) and B ( 1b ) ( trans -isomers). The absolute configuration of all optically pure compounds was determined by using NMR and comparing their electronic circular dichroism data with model compounds of known absolute configurations. Mechanisms for cis – trans -isomerization of silybin are proposed and supported by quantum mechanical calculations. Beilstein J. Org. Chem. 2014, 10, 1047–1063. doi:10.3762/bjoc.10.105
Keywords:
2,3-cis-silybin10,11-cis-silybinisomerizationsilibininsilybinsilymarin
Electronic ISSN:
1860-5397
Topics:
Chemistry and Pharmacology
Permalink