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Naphtho[2,3-c]pyran-5,10-quinones. Syntheses of the racemates of quinone A, quinone A′, and deoxyquinone A dimethyl ethers of 7-methoxyeleutherin, and of isoeleutherin

Giles, R.G.F., Green, I.R., Hugo, V.I., Mitchell, P.R.K. and Yorke, S.C. (1984) Naphtho[2,3-c]pyran-5,10-quinones. Syntheses of the racemates of quinone A, quinone A′, and deoxyquinone A dimethyl ethers of 7-methoxyeleutherin, and of isoeleutherin. Journal of the Chemical Society, Perkin Transactions 1 . pp. 2383-2388.

Link to Published Version: http://dx.doi.org/10.1039/P19840002383
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Abstract

Treatment of 3-(1-hydroxyethyl)-1,4,5,7-tetrarmethoxy-2-prop-2-enylnaphthalene (33) with potassium t-butoxide in dimethylformamide under nitrogen for a short time gave a high yield of trans-3,4-dihydro-5,7,9,10-tetramethoxy-1,3-dimethyl-1H-naphtho[2,3-c]pyran (41). This compound, with the same base and solvent, but in air, afforded a mixture comprising its cis-epimer (42), together with the two possible 4-hydroxy derivatives, namely (35) and (38). Silver(II) oxide oxidation of compounds (35), (38), (41), and (42) gave, respectively, the dimethyl ethers of quinone A, quinone A′, and deoxyquinone A, and also 7-methoxyeleutherin.

Publication Type: Journal Article
Publisher: Royal Society of Chemistry
Copyright: © 1984 Royal Society of Chemistry
URI: http://researchrepository.murdoch.edu.au/id/eprint/35675
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