Canadian Journal of Chemistry

C-Alkylation of 1, 3-dihydroxyanthraquinones. Total syntheses of (±)-averufin and (±)-bipolarin

A Castonguay, P Brassard

Index: Castonguay,A.; Brassard,P. Canadian Journal of Chemistry, 1977 , vol. 55, p. 1324 - 1332

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Citation Number: 30

Abstract

Various methods of substituting 1, 3-dihydroxyanthraquinones in the 2-position were investigated. It was eventually found that direct hydroxyalkylation in the presence of definite amounts of sodium bicarbonate could be carried out. The reaction of 1, 3, 6, 8- tetrahydroxyanthraquinone with 5-oxohexanal or 4-hydroxybutanal gave, respectively, among other products,(±)-averufin and (±)-bipolarin.