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Approaches to the synthesis of 4-hydroxypiloquinone

Giles, R.G.F., Mitchell, P.R.K. and Sargent, M.V. (1983) Approaches to the synthesis of 4-hydroxypiloquinone. Journal of the Chemical Society, Perkin Transactions 1 . pp. 2147-2152.

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The synthesis of 4-acetoxy-1,8-dihydroxy-2-methyl-3-(4-methylpentanoyl)phenanthrene-9,10-quinoee (30) and 1,4,8-trimethoxy-2-methyl-3-(4-methylpentanoyl)phenanthrene-9,10-quinone (33), derivatives of the mould metabolite 4-hydroxypiloquinone [1,4,8-trihydroxy-2-methyl-3-(4-methylpentanoyl)-phenanthrene-9,10-quinone](2) are described. Photocyclization of methyl 2,2′,5,6′-tetramethoxy-3-methylstilbene-4-carboxylate (21) provided methyl 1,4,8-trimethoxy-2-methylphenanthrene-3-carboxylate (22), suitable for further elaboration into the natural derivatives.

Item Type: Journal Article
Publisher: Royal Society of Chemistry
Copyright: © 1983 Royal Society of Chemistry
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