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

Autor:	Su Young Han, Hyun Suck Lee, Jung Woon Hwang, Deok Mo Yang, Jong-Gab Jun, Da Hye Choi
Rok vydání:	2009
Předmět:	Piceatannol chemistry.chemical_classification chemistry.chemical_compound chemistry Yield (chemistry) Wittig reaction Total synthesis General Medicine Triphenylphosphine Medicinal chemistry Phosphonate Aldehyde Tetrahydrofuran
Zdroj:	ChemInform. 40
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200938206
Popis:	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 1 h to give 99% yield of single (E)-stilbene.
Databáze:	OpenAIRE
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