Reactions of keten acetals. Part 7. Total syntheses of the tetramethyl ethers of the 1-acyl-2,4,5,7-tetrahydroxyanthraquinones rhodolamprometrin and rhodocomatulin
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 17,p. 1852-1856
- https://doi.org/10.1039/p19760001852
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.Keywords
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