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
收藏
页码：1425 / 1432
页数：8
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