• Bulletin of the Korean Chemical Society
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• v.25 no.11
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• pp.1720-1722
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• 2004

• Bulletin of the Korean Chemical Society
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• v.21 no.12
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• pp.1263-1266
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• 2000

• Bulletin of the Korean Chemical Society
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• v.21 no.3
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• pp.355-357
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• 2000

• Journal of the Korean Chemical Society
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• v.37 no.1
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• pp.141-147
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• 1993

A brief route for total synthesis of 6-deoxybisanhydrodaunomycinone(20) was described, namely the precursor of the daunomycinone, the aglycone of the anticancer antibiotic daunorubicin (1b). The prepared enone 4 was condensed with phthalide sulfone 7 to afford anthraquinone 10 after oxidation and methylation. The benzylic group of 10 was brominated, and subsequent oxidation with bis(tetrabutylammonium) dichromate followed by cyclization give hydroxyanthraquinone 16, which was displaced with thiophenol. Oxidation of 17 with m-CPBA in phosphate buffer solution afforded anthraquinonyl sulfone 18 which was condensed with methyl vinyl ketone (19) to furnish 20.

• Bulletin of the Korean Chemical Society
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• v.9 no.1
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• pp.13-15
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• 1988

Several types of resocinols have been monobrominated in the ring in good yields with sodium bromide in the presence of 18-crown-6 on oxidation with m-chloroperbenzoic acid. Monoiodination takes place with 2'-(1-methylcyclohexen-3-yl)-5-(1,1-dimethylheptyl )-resocinol when sodium iodide is employed. This new reagent system, MX/18-crown-6/m-CPBA (M =$K^+, Na^+, X = Br^-, I^-X$ ), effects the regiospecific halogenation of activated aromatic ring over olefinic double bond.

• Journal of the Korean Chemical Society
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• v.40 no.9
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• pp.615-622
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• 1996

(Benzotriazol-1-yl)arenesulfonylalkanes, 2a, 2b, 3a and 3b, were prepared by lithiation of 1-(benzotriazol-1-yl)arenesulfonylmethanes followed by reaction with alkyl iodides. Very bulky molecules such as 1,1-di(benzotriazol-1-yl)-1-aryl-1-thiophenoxymethanes 5, 1,1-di(benzotriazol-1-yl)-1-thiophenoxymethane 9a and 1,1-di(benzotriazol-1-yl)-1,1-dithiophenoxymethane 9b were synthesized. 1,1-Di(benzotriazol-1-yl)-1-benzenesulfoxymethane 10a and 1,1-di(benzotriazol-1-yl)-1-benzenesulfonylmethane 10b were also synthesized by the oxidation of compound 9a, while oxidation of sulfide group on compound 5 and 9b by m-CPBA were not successful. On the other hand, pyrolysis and hydrolysis of 3-(benzotriazol-1-yl)-3-toluenesulfonylpentane 3b gave 3-toluenesulfonyl-2-pentene 11 and diethyl ketone 13a, respectively, which means there are both C-N and C-S bond cleavages.