期刊
SYNTHETIC COMMUNICATIONS
卷 39, 期 8, 页码 1425-1432出版社
TAYLOR & FRANCIS INC
DOI: 10.1080/00397910802528944
关键词
(E)-Selective Wittig-Horner reaction; piceatannol; polyphenol; stilbene
资金
- Basic Research Program of Korea Science and Engineering Foundation [R01-2007-000-20164-0]
- Ministry of Commerce, Industry
- Energy through the Center for Efficacy Assessment and Development of Functional Foods and Drugs at Hallym University
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.
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