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

被引：55

作者：

Ferré-Filmon, K ^{[1
]}

Delaude, L ^{[1
]}

Demonceau, A ^{[1
]}

Noels, AF ^{[1
]}

机构：

[1] Univ Liege, Inst Chim, CERM, B-4000 Cointe Ougree, Belgium

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 15期

关键词：

alkenes; homogeneous catalysis; natural products; resveratrol; ruthenium;

D O I：

10.1002/ejoc.200500068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 & Co. KGaA, 69451 Weinheirn, Germany, 2005).

引用

页码：3319 / 3325

页数：7

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