- Dimeric Naphthoquinones, XVIII. - Ammonium Cerium(IV) Nitrate as Oxidising Agent: peri-Hydroxylation of Juglones giving Naphthazarins
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5,8-Dialkoxy-1-naphthols (type 6a) which are easily accessible starting from juglones (5a) are oxidised under mild conditions using ammonium cerium(IV) nitrate, yielding with high p-selectivity the corresponding 1,4-naphthoquinones (7a).By dealkylation of the latter, substituted 1,8-dihydroxy-1,4-naphthoquinones (1a) are obtained in good yields.
- Laatsch, Hartmut
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p. 1655 - 1668
(2007/10/02)
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- Dimeric Naphthoquinones, IX. - Isodiospyrin and Elliptinone. - Synthesis of 6,6'-Dimeric Bijuglones by Phenol Oxidation
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Oxidative coupling of the naphthol 37a gave the potential natural product 7,7'-dimethyl-6,6'-bijuglone (5) and, in lower yield, isodiospyrin (21).Regiospecific syntheses of 5, elliptinone (10), and 6,6'-bijuglone (45a) were achieved by phenol oxidation of suitable substituted p-chloronaphthols.
- Laatsch, Hartmut
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p. 319 - 339
(2007/10/02)
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