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Synthesis and acetylation of naphthols as precursors to naturally derived naphthoquinones; crystal structure of the aphin-related 7-O-methyl quinone A

Giles, R.G.F., Green, I.R., Niven, M.L. and Yorke, S.C. (1988) Synthesis and acetylation of naphthols as precursors to naturally derived naphthoquinones; crystal structure of the aphin-related 7-O-methyl quinone A. Journal of the Chemical Society, Perkin Transactions 1 (8). pp. 2459-2467.

Link to Published Version: http://dx.doi.org/10.1039/P19880002459
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Abstract

A route is described to 1,5,7-trialkoxy-4-naphthols. A method has been established to convert these compounds into the corresponding 3-acetyl-4-naphthols, in good yield, with a view to synthesizing naturally derived naphtho[2,3-c]pyran-5,10-quinones. Boron trichloride-induced monodemethylation of racemic Quinone A dimethyl ether was effected without perturbation of the pyran ring stereochemistry; this was confirmed by an X-ray crystallographic investigation.

Publication Type: Journal Article
Publisher: Royal Society of Chemistry
Copyright: © 1988 Royal Society of Chemistry
URI: http://researchrepository.murdoch.edu.au/id/eprint/35692
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