Cis-trans isomerization of silybins A and B
2014 (English)In: Beilstein Journal of Organic Chemistry, ISSN 2195-951X, E-ISSN 1860-5397, Vol. 10, 1047-1063 p.Article in journal (Refereed) Published
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-OEt2) 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. © 2014 Novotná et al; licensee Beilstein-Institut.
Place, publisher, year, edition, pages
Beilstein-Institut , 2014. Vol. 10, 1047-1063 p.
10, 11-cis-silybin; 2, 3-cis-silybin; Isomerization; Silibinin; Silybin; Silymarin
IdentifiersURN: urn:nbn:se:liu:diva-116387DOI: 10.3762/bjoc.10.105PubMedID: 24991256ScopusID: 2-s2.0-84901370892OAI: oai:DiVA.org:liu-116387DiVA: diva2:798664
Funding Agencies|P207/10/0288, GACR, Czech Science Foundation2015-03-272015-03-262015-10-22