Total Synthesis of (±)-Agastinol

Total Synthesis of (±)-Agastinol

A synthesis of the tetrahydrofuran lignan (±)-agastinol, starting from the cheap Vanillin, has been developed based on Stobbe reaction with diethyl succinate to give the skeleton of lignan, which was then reduced to afford meso- and threo-(±)-secoisolanciresinol. threo-(±)-Secoisolanciresinol was tr...

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Veröffentlicht in:Journal of chemical research 2011-06, Vol.35 (6), p.352-354
Hauptverfasser: Ding, Junwei, Zhou, Haitang, Jiao, Bin, Xia, Yamu
Format: Artikel
Sprache:eng
Schlagworte:
Acetic acid
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Zusammenfassung:A synthesis of the tetrahydrofuran lignan (±)-agastinol, starting from the cheap Vanillin, has been developed based on Stobbe reaction with diethyl succinate to give the skeleton of lignan, which was then reduced to afford meso- and threo-(±)-secoisolanciresinol. threo-(±)-Secoisolanciresinol was treated with DDQ in acetic acid to give the 2-aryl tetrahydrofuran lignan, and which was then condensed with ferulic acid to give (±)-agastinol for the first time.
ISSN:1747-5198
2047-6507
DOI:10.3184/174751911X13082938433857