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A short, convergent synthesis of aristolindiquinone

Botha, M.E., Giles, R.G.F. and Yorke, S.C. (1991) A short, convergent synthesis of aristolindiquinone. Journal of the Chemical Society, Perkin Transactions 1 (1). p. 85.

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Aristolindiquinone, 2,5-dihydroxy-3,8-dimethyl-1,4-naphthoquinone 1, is synthesised by the regiochemical addition of 1-methoxy-1-trimethylsiloxypenta-1, 3-diene 2 to 5-bromo-2-methoxy-3methyl-1,4-benzoquinone 3. The regioisomer 2,8-dihydroxy-3,5-dimethyl-1,4-naphthoquinone 4 is prepared by reaction of the same diene 2 with 2-methoxy-3-methyl-1,4-benzoquinone 11. The former reaction readily provided sufficient quantities of aristolindiquinone 1 for biological evaluation for fertility regulation in rats, for which purpose it was found to be inactive.

Item Type: Journal Article
Publisher: Chemical Society
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