Issue 0, 1980
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Benzodioxans by oxidative phenol coupling. Synthesis of silybin

Lucio Merlini,   Antonio Zanarotti,   Andrew Pelter,   Malcolm P. Rochefort  and  Rudolf Hänsel  

Abstract

Oxidative coupling of substituted catechols with isoeugenol or coniferyl alcohol in the presence of silver oxide affords 2,3-trans-1,4-benzodioxans in good yield. The reaction is highly regioselective when the catechol bears an alkyl substituent, much less so in the case of an electrophilic one. A free-radical coupling mechanism is proposed. A one-step biomimetic synthesis in high yield of the natural flavanolignans silybin and isosilybin from 2R,3R-dihydroquercetin and coniferyl alcohol is reported.

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Article information

DOI
https://doi.org/10.1039/P19800000775
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1980, 775-778

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Benzodioxans by oxidative phenol coupling. Synthesis of silybin

L. Merlini, A. Zanarotti, A. Pelter, M. P. Rochefort and R. Hänsel, J. Chem. Soc., Perkin Trans. 1, 1980, 775 DOI: 10.1039/P19800000775

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