Efficient Total Synthesis of Piceatannol via (E)-Selective Wittig-Horner Reaction

被引：21

作者：

Han, Su Young

Lee, Hyun Suck

Choi, Da Hye

Hwang, Jung Woon

Yang, Deok Mo

Jun, Jong-Gab ^{[1
]}

机构：

[1] Hallym Univ, Dept Chem, Chunchon 200702, South Korea

来源：

SYNTHETIC COMMUNICATIONS | 2009年 / 39卷 / 08期

关键词：

(E)-Selective Wittig-Horner reaction; piceatannol; polyphenol; stilbene; PRODUCT; RESVERATROL;

D O I：

10.1080/00397910802528944

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient and practical total synthesis of piceatannol via (E)-selective Wittig-Horner reaction is demonstrated with six steps in overall 40% yield from a commercially available, cheap starting material, 3,5-dihydroxybenzoic acid. Wittig-Horner reaction of diethyl phosphonate with aldehyde showed a superior (E)-selectivity compare to Wittig reaction using triphenylphosphine. We optimized the Wittig-Horner reaction condition by using NaH (6 equiv) in tetrahydrofuran (THF) at reflux 1h to give 99% yield of single (E)-stilbene.

引用

页码：1425 / 1432

页数：8

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