Synthesis 2014; 46(02): 170-174
DOI: 10.1055/s-0033-1338559
paper
© Georg Thieme Verlag Stuttgart · New York

The First Synthesis of Uralenol, 5′-Prenylated Quercetin, via Palladium-Catalyzed­ O-Dimethylallylation Reaction with Concurrent Acetyl Migration

Tomoyuki Kawamura
a   Department of Pharmaceutical Chemistry, Division of Heath Biosciences, Graduate School of the University of Tokushima, 1-78-1, Sho-machi, Tokushima 770-8505, Japan   Fax: +81(88)6337284   Email: nem@ph.tokushima-u.ac.jp
,
Moemi Hayashi
a   Department of Pharmaceutical Chemistry, Division of Heath Biosciences, Graduate School of the University of Tokushima, 1-78-1, Sho-machi, Tokushima 770-8505, Japan   Fax: +81(88)6337284   Email: nem@ph.tokushima-u.ac.jp
,
Rie Mukai
b   Department of Food Science, Institute of Health Biosciences, Graduate School of the University of Tokushima, 3-18-15, Kuramoto-cho, Tokushima 770-8503, Japan
,
Junji Terao
b   Department of Food Science, Institute of Health Biosciences, Graduate School of the University of Tokushima, 3-18-15, Kuramoto-cho, Tokushima 770-8503, Japan
,
Hisao Nemoto*
a   Department of Pharmaceutical Chemistry, Division of Heath Biosciences, Graduate School of the University of Tokushima, 1-78-1, Sho-machi, Tokushima 770-8505, Japan   Fax: +81(88)6337284   Email: nem@ph.tokushima-u.ac.jp
› Author Affiliations
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Publication History

Received: 18 September 2013

Accepted after revision: 25 October 2013

Publication Date:
22 November 2013 (online)


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Abstract

The first synthesis of uralenol, 5′-prenylated quercetin, is described. The key step is a palladium-catalyzed O-1,1-dimethylallylation reaction, with concurrent acetyl migration to afford the desired intermediate as a major isomer, which was purified by recrystallization. Finally, Claisen rearrangement, followed by deprotection of all phenolic protecting groups, afforded uralenol in excellent yield.

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