Issue 17, 1976
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Reactions of keten acetals. Part 7. Total syntheses of the tetramethyl ethers of the 1-acyl-2,4,5,7-tetrahydroxyanthraquinones rhodolamprometrin and rhodocomatulin

Jacques Banville  and  Paul Brassard  

Abstract

Acylketen acetals or (better) their trimethylsilyl enol ethers condense regiospecifically with 2-halogeno-1,4-naphthoquinones. Reactions of 1,1-dimethoxy-3-trimethylsilyloxyhexa-1,3-diene and -octa-1,3-diene with 2-chloro-6,8-dimethoxy-1,4-naphthoquinone gave the corresponding 1-alkyl-2,4,5,7-tetramethoxyanthraquinones. The latter underwent spontaneous photochemical oxidation at the benzylic position and yielded the title compounds. The method has been adapted to provide a simple synthesis of questin.

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Article information

DOI
https://doi.org/10.1039/P19760001852
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1976, 1852-1856

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Reactions of keten acetals. Part 7. Total syntheses of the tetramethyl ethers of the 1-acyl-2,4,5,7-tetrahydroxyanthraquinones rhodolamprometrin and rhodocomatulin

J. Banville and P. Brassard, J. Chem. Soc., Perkin Trans. 1, 1976, 1852 DOI: 10.1039/P19760001852

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