61836-43-9Relevant academic research and scientific papers
Oxidative coupling of methoxynaphthylenediols
Maiti, Bhim C.,Musgrave, Oliver C.,Skoyles, Douglas
, p. 6568 - 6574 (2007/10/03)
The oxidative coupling of a mixture of 1-methoxy-7-methyl-4,5- naphthylenediol and 4-methoxy-7-methyl-1,5-naphthylenediol using lead(IV) oxide gives the symmetrical bisnaphthalene indigos diosindigo A and diosindigo B together with the corresponding unsymmetrical isomer. Oxidation of the first two by nitric acid gives the binaphthyldiquinones mamegakinone and biramentaceone, respectively; the third gives the unsymmetrical diquinone rotundiquinone. Similar oxidations of related naphthylenediols are described.
Aerobic oxidative dimerization of 1-naphthols to 2,2′- binaphthoquinones mediated by SnCl4 and its application to natural product synthesis
Takeya, Tetsuya,Doi, Hirohisa,Ogata, Tokutaro,Okamoto, Iwao,Kotani, Eiichi
, p. 9049 - 9060 (2007/10/03)
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.
SnCl4-mediated oxidative reaction for formation of binaphthoquinone and dinaphthofuran frameworks and its application to natural product synthesis
Ogata, Tokutaro,Okamoto, Iwao,Doi, Hirohisa,Kotani, Eiichi,Takeya, Tetsuya
, p. 2041 - 2044 (2007/10/03)
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.
A facile synthesis of naturally occurring binaphthoquinones: Efficient oxidative dimerization of 4-alkoxy-1-naphthols using silver(II) oxide-40% nitric acid
Tanoue, Yasuhiro,Sakata, Kazunori,Hashimoto, Mamoru,Morishita, Shin-Ich,Hamada, Moritsugu,Kai, Norihisa,Nagai, Takeshi
, p. 99 - 104 (2007/10/03)
Oxidation of 4-alkoxy-1-naphthols with AgO-40% HNO3 occurred along with a dimerization to give the corresponding bi-1,4-naphthoquinones. The oxidative dimerization required one hydroxyl group and took place at its ortho position. This reaction was applicable to syntheses of naturally occurring binaphthoquinones, bivitamin K3 and 3,3′-bijuglone.
Regioselective Syntheses of 3,3'-Bijuglone, Mamegakinone, Dianellinone, cyclo-Trijuglone, Xylospyrin, and Trianellinone by Phenol-Quinone Addition
Brockmann, Hans,Laatsch, Hartmut
, p. 433 - 447 (2007/10/02)
Regioselective phenol-quinone addition of juglone (1a), 7-methyljuglone (1b), and stypandrone (1c) in pyridine yields the dimers 3,3-bijuglone (5a), mamegakinone (5c), and dianellinone (5e).In acetic acid mainly the cyclo trimers cyclo-trijuglone (12a), xylospyrin (12d), and trianellinone (12g) are obtained.
Dimeric Naphthoquinones, IV1). - Synthesis of Biramentaceone, Mamegakinone and Rotundiquinone
Laatsch, Hartmut
, p. 1321 - 1347 (2007/10/02)
Mamegakinone (8a), biramentaceone (12a), 3,3'-bijuglone (8b), 2,2-bijuglone (12b) and their methyl ethers were prepared by oxidative coupling of substituted 4-methoxy-1-naphthols; indigoids like 24 are intermediates.Cooxidation of the isomeric dimethoxy-1
