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Synthesis 2018; 50(23): 4611-4616
DOI: 10.1055/s-0037-1609554
DOI: 10.1055/s-0037-1609554
paper
DDQ-Mediated Oxidation of Allylarenes: Expedient Access to Cinnamaldehyde-Containing Phenylpropanoids
Authors
Financial support from National Natural Science Foundation of China (No. 21702002 and 31640068), and Anhui Provincial Natural Science Foundation (1808085QC79) is gratefully acknowledged.
Further Information
Publication History
Received: 12 May 2018
Accepted after revision: 13 June 2018
Publication Date:
24 July 2018 (online)
Abstract
Phenylpropanoid natural products containing a cinnamaldehyde motif were easily synthesized from allylarenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation. Representative examples described herein are five types of 4-hydroxycinnamaldehyde derivatives from monolignols biosynthesis, Boropinal C, and 7-methoxywutaifuranal from plant extracts. Especially, simple synthesis of 7-methoxywutaifuranal was exploited through selective mono-oxidation and subsequent isomerization–ring-closing-metathesis strategy.
Key words
phenylpropanoids - DDQ oxidation - 4-hydroxycinnamaldehydes - boropinal C - 7-methoxywutaifuranalSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609554.
- Supporting Information (PDF)
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