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1 article(s) from Gažák, Radek

cis–trans Isomerization of silybins A and B

Michaela Novotná,
Radek Gažák,
David Biedermann,
Florent Di Meo,
Petr Marhol,
Marek Kuzma,
Lucie Bednárová,
Kateřina Fuksová,
Patrick Trouillas and
Vladimír Křen

Beilstein J. Org. Chem. 2014, 10, 1047–1063, doi:10.3762/bjoc.10.105

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Graphical Abstract

Figure 1: Selected naturally occurring trans-silybins and their acetates.

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Figure 2: Isosilybins occurring as minor components of silymarin.

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Figure 3: Structures of cis-derivatives obtained by the isomerization of 1 using BF₃·OEt₂ in EtOAc.

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Scheme 1: Silybin A and silybin B isomerizations into their 2,3-cis-isomers (DMF).

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Scheme 2: Silybin B isomerization in EtOAc.

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Scheme 3: Isomerization of silybin A in EtOAc.

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Scheme 4: Schematic flowchart of the procedures for the preparation and the isolation of cis-silybin isomers (...

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Figure 4: ECD spectrum of silybin B (1b) and its separation (in a crude approximation) into two π-conjugated ...

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Figure 5: Synthetic and natural (benzodioxane-type) compounds related to silybin stereoisomers with known abs...

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Scheme 5: Proposed mechanisms of Lewis acid catalyzed isomerization at the benzopyranone ring of 23-O-acetyls...

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Figure 6: Taxillusin, (2R,3R)-taxifolin 3-β-D-glucopyranoside 6''-gallate (24).

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Scheme 6: Proposed mechanism of Lewis acid catalyzed isomerization of benzodioxane part of 23-O-acetylsilybin...

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Figure 7: Spatial distribution of nucleophilic f−(r) (blue) and electrophilic f+(r) (blue) Fukui functions of...

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Published 08 May 2014

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