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Synthesis 2006(2): 273-278  
DOI: 10.1055/s-2005-918506
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Simple Access to Biologically Important trans-Stilbenes via Ru-Catalyzed Cross Metathesis

Janna Velder, Stefanie Ritter, Johann Lex, Hans-Günther Schmalz*
Institute of Organic Chemistry, Universität zu Köln, Greinstrasse 4, 50939 Cologne, Germany
Fax: +49(221)4703064; e-Mail: schmalz@uni-koeln.de;
Further Information

Publication History

Received 21 June 2005
Publication Date:
21 December 2005 (online)

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Abstract

The cross metathesis of methoxy- or acetoxy-substituted styrenes using the Grubbs II catalyst affords unsymmetrical (mixed) E-stilbenes with astonishingly high selectivity (up to 79% yield). This approach offers a short and flexible synthesis of variously substituted stilbenes, which are derivatives or precursors of biologically important compounds such as resveratrol, piceatannol, and pinostilbene.

Key words

cross metathesis - ruthenium catalysis - resveratrol - stilbenes

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