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Synthesis 2014; 46(02): 170-174
DOI: 10.1055/s-0033-1338559
DOI: 10.1055/s-0033-1338559
paper
The First Synthesis of Uralenol, 5′-Prenylated Quercetin, via Palladium-Catalyzed O-Dimethylallylation Reaction with Concurrent Acetyl Migration
Further Information
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information