A short, convergent synthesis of aristolindiquinone
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 85-88
- https://doi.org/10.1039/p19910000085
Abstract
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-3-methyl-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.Keywords
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