DDQ-Mediated Oxidation of Allylarenes: Expedient Access to 
Cinnamaldehyde-Containing Phenylpropanoids

Tao-Shan Jiang; Qingqing Zhang; Guohui Li; Xi Cheng; Yongping Cai

doi:10.1055/s-0037-1609554

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(23): 4611-4616
DOI: 10.1055/s-0037-1609554

paper

DDQ-Mediated Oxidation of Allylarenes: Expedient Access to Cinnamaldehyde-Containing Phenylpropanoids

Authors

Tao-Shan Jiang *

School of Life Sciences, Anhui Agricultural University, Hefei, 230036, P. R. of China eMail: jts2015@ahau.edu.cn eMail: ypcaiah@163.com
Qingqing Zhang

School of Life Sciences, Anhui Agricultural University, Hefei, 230036, P. R. of China eMail: jts2015@ahau.edu.cn eMail: ypcaiah@163.com
Guohui Li

School of Life Sciences, Anhui Agricultural University, Hefei, 230036, P. R. of China eMail: jts2015@ahau.edu.cn eMail: ypcaiah@163.com
Xi Cheng

School of Life Sciences, Anhui Agricultural University, Hefei, 230036, P. R. of China eMail: jts2015@ahau.edu.cn eMail: ypcaiah@163.com
Yongping Cai*

School of Life Sciences, Anhui Agricultural University, Hefei, 230036, P. R. of China eMail: jts2015@ahau.edu.cn eMail: ypcaiah@163.com

Abstract

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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-methoxywutaifuranal

Volltext

Referenzen

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