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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Intramolecular Oxidative Coupling of Aromatic Compounds. I. Oxidation of Diphenolic Substrates

AS Krauss and WC Taylor

Australian Journal of Chemistry 44(9) 1307 - 1333
Published: 1991

Abstract

The synthesis of (2RS,3SR)-1-(3,5-dihydroxy-4-methoxyphenyl)-(4-hydroxy-3,5-dimethoxy-phenyl)-2,3-dimethylbutan-1-one (26) is described. Diphenolic oxidative coupling of (26) did not produce a eupodienone -type product. An aryltetralin derivative was formed instead by aryl-benzyl coupling and was further oxidized to the novel oxa spiro dienone (63). The acetoxy compound (71) derived by reduction of the carbonyl group in (26) gave a similar product (72).

https://doi.org/10.1071/CH9911307

© CSIRO 1991

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