cis–trans Isomerization of silybins A and B

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...

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Autores principales: Novotná, Michaela, Gažák, Radek, Biedermann, David, Di Meo, Florent, Marhol, Petr, Kuzma, Marek, Bednárová, Lucie, Fuksová, Kateřina, Trouillas, Patrick, Křen, Vladimír
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077359/
https://www.ncbi.nlm.nih.gov/pubmed/24991256
http://dx.doi.org/10.3762/bjoc.10.105
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author Novotná, Michaela
Gažák, Radek
Biedermann, David
Di Meo, Florent
Marhol, Petr
Kuzma, Marek
Bednárová, Lucie
Fuksová, Kateřina
Trouillas, Patrick
Křen, Vladimír
author_facet Novotná, Michaela
Gažák, Radek
Biedermann, David
Di Meo, Florent
Marhol, Petr
Kuzma, Marek
Bednárová, Lucie
Fuksová, Kateřina
Trouillas, Patrick
Křen, Vladimír
author_sort Novotná, Michaela
collection PubMed
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.
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spelling pubmed-40773592014-07-02 cis–trans Isomerization of silybins A and B Novotná, Michaela Gažák, Radek Biedermann, David Di Meo, Florent Marhol, Petr Kuzma, Marek Bednárová, Lucie Fuksová, Kateřina Trouillas, Patrick Křen, Vladimír Beilstein J Org Chem Full Research Paper 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-Institut 2014-05-08 /pmc/articles/PMC4077359/ /pubmed/24991256 http://dx.doi.org/10.3762/bjoc.10.105 Text en Copyright © 2014, Novotná et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Novotná, Michaela
Gažák, Radek
Biedermann, David
Di Meo, Florent
Marhol, Petr
Kuzma, Marek
Bednárová, Lucie
Fuksová, Kateřina
Trouillas, Patrick
Křen, Vladimír
cis–trans Isomerization of silybins A and B
title cis–trans Isomerization of silybins A and B
title_full cis–trans Isomerization of silybins A and B
title_fullStr cis–trans Isomerization of silybins A and B
title_full_unstemmed cis–trans Isomerization of silybins A and B
title_short cis–trans Isomerization of silybins A and B
title_sort cis–trans isomerization of silybins a and b
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077359/
https://www.ncbi.nlm.nih.gov/pubmed/24991256
http://dx.doi.org/10.3762/bjoc.10.105
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