Benzodioxans by oxidative phenol coupling. Synthesis of silybin
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 775-778
- https://doi.org/10.1039/p19800000775
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.This publication has 1 reference indexed in Scilit: