- Aerobic oxidative dimerization of 1-naphthols to 2,2′- binaphthoquinones mediated by SnCl4 and its application to natural product synthesis
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We developed a simple method for the direct synthesis of 2,2′-binaphthoquinones, utilizing oxidative dimerization via electron donor-acceptor complex formation of 1-naphthols with SnCl4 in the presence of dioxygen. This oxidation involves a catalytic cycle of SnCl 4, and the reaction mechanism is discussed. As an application of this method to natural products synthesis, we describe facile biomimetic syntheses of the binaphthoquinones 3,3′-bijuglone, 3,3′-biplumbagin and elliptinone.
- Takeya, Tetsuya,Doi, Hirohisa,Ogata, Tokutaro,Okamoto, Iwao,Kotani, Eiichi
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- SnCl4-mediated oxidative reaction for formation of binaphthoquinone and dinaphthofuran frameworks and its application to natural product synthesis
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A simple method was developed for the direct synthesis of 2,2′-binaphthoquinones and dinaphtho[1,2-b;2′,1′-d]furans, utilizing an oxidative reaction via electron donor-acceptor complexes of 1-naphthols with SnCl4 in the absence or presence of dioxygen. As an application of this method to natural product synthesis, we describe a facile biomimetic synthesis of several binaphthoquinones, 3,3′-bijuglone, 3,3′-biplumbagin and elliptinone.
- Ogata, Tokutaro,Okamoto, Iwao,Doi, Hirohisa,Kotani, Eiichi,Takeya, Tetsuya
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- Dimeric Naphthoquinones, XVI. - Synthesis of Maritinone and Other 8,8'-Bijuglones
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Maritinone (3a) and the structure-analogous 8,8'-bijuglones 3b and 4b were obtained by phenol oxidation of suitably substituted 2-bromo-1-naphthols.In side reactions, dinaphthopyrans 24 were formed which are possible intermediates or side products in the biosynthesis of unsymmetrically 6,8'-linked binaphthoquinones.
- Laatsch, Hartmut
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p. 2420 - 2442
(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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