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2 article(s) from Biedermann, David

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

Guozheng Huang,
Simon Schramm,
Jörg Heilmann,
David Biedermann,
Vladimír Křen and
Michael Decker

Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66

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Figure 1: Structures of silibinin, isosilybin, and silychristin, and hydnocarpin-type flavonolignans.

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Figure 2: Synthetic strategy of semi-synthesis of hydnocarpins from silybins [22].

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Scheme 1: Synthesis of ester derivatives of silibinin and conversion to hydnocarpin-type compounds. Reaction ...

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Figure 3: Putative mechanism of dehydration of flavanonols under Mitsunobu conditions.

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Scheme 2: Attempt to dehydrate catechin. Reagents and conditions: a) p-nitrobenzoic acid, Ph₃P, DIAD, THF, rt...

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Scheme 3: Preparation of hydnocarpin (4) and isohydnocarpin (6) and attempt to dehydrate silydianin A (11). R...

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Published 08 Apr 2016

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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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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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