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DOI: 10.1039/A808884E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 461-464

A novel type of spiro compound formed by oxidative cross coupling of methyl sinapate with a syringyl lignin model compound. A model system for the β-1 pathway in lignin biosynthesis

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Harri Setälä, Aarne Pajunen, Petteri Rummakko, Jussi Sipilä and Gösta Brunow

Abstract

Oxidative coupling of methyl (E[hair space])-sinapate with 1-(4-hydroxy-3,5-dimethoxyphenyl)ethanol, a syringyl lignin model compound, was carried out with hydrogen peroxide catalyzed by horseradish peroxidase. The main product was a cyclohexadienone spiro compound of a novel type. Mild acidolysis caused the loss of one side chain and yielded a dimeric compound with a 1,2-diarylpropane structure. This is the first example of the formation of this structural type by oxidative coupling in vitro.

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