Stereoselective synthesis of (E)-hydroxystilbenoids by ruthenium-catalyzed cross-metathesis

Ferre-Filmon, Karine; Delaude, Lionel; Demonceau, Albert; Noels, Alfred

doi:10.1002/ejoc.200500068

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Stereoselective synthesis of (E)-hydroxystilbenoids by ruthenium-catalyzed cross-metathesis

Ferre-Filmon, Karine; Delaude, Lionel; Demonceau, Albert et al.

2005 • In European Journal of Organic Chemistry, (15), p. 3319-3325

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10.1002/ejoc.200500068

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Keywords :

alkenes; homogeneous catalysis; natural products; resveratrol; ruthenium

Abstract :

[en] An efficient and highly stereoselective synthetic procedure is reported for the construction of symmetrical and unsymmetrical (E)-polymethoxystilbene and (E)-polyhydroxystilbene derivatives. The strategy rests on a cross-metathesis reaction catalyzed by stable, well-defined (alkylidene)ruthenium complexes, in particular the second-generation Grubbs catalyst [RuCl2(=CHPh)(SlMes)(PCY3)1 [SIMes = 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]. The metathesis of unprotected phenolic styrenes is illustrated by the synthesis of the important phytoalexins (E)-3,4',5-trihydroxystilbene (resveratrol) and (E)-3,3',4,5'-tetrahydroxystilbene (piceatannol). (c) Wiley-VCH Verlag GmbH

Disciplines :

Chemistry

Author, co-author :

Ferre-Filmon, Karine

Delaude, Lionel ; Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique

Demonceau, Albert ; Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique

Noels, Alfred ; Université de Liège - ULiège > Services généraux (Faculté des sciences) > Relations académiques et scientifiques (Sciences)

Language :

English

Title :

Stereoselective synthesis of (E)-hydroxystilbenoids by ruthenium-catalyzed cross-metathesis

Publication date :

2005

Journal title :

European Journal of Organic Chemistry

ISSN :

1434-193X

eISSN :

1099-0690

Publisher :

Wiley-VCH Verlag Gmbh, Weinheim, Germany

Issue :

Pages :

3319-3325

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 26 June 2009

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