- Boron-selective biaryl coupling approach to versatile dibenzoxaborins and application to concise synthesis of defucogilvocarcin M
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An efficient synthetic method for versatile dibenzoxaborins based on boron-selective Suzuki-Miyaura cross-coupling between o-borylphenols and aryl halides or triflates bearing a 1,8-diaminonaphthalene-protected o-boryl group is reported. A short synthesis
- Sumida, Yuto,Harada, Ryu,Kato-Sumida, Tomoe,Johmoto, Kohei,Uekusa, Hidehiro,Hosoya, Takamitsu
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supporting information
p. 6240 - 6243
(2015/01/09)
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- One step hair coloring compositions using salts
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A hair coloring composition comprising the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an amino phenol, a naphthol, a polyhydric phenol, a catechol and mixtures thereof; wherein the composition comprising one or more oxidative hair coloring agents further comprises al least one water soluble carbonate releasing salts; and optionally a water soluble ammonium salt, is described.
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- Enhanced color deposition for hair with sequestering agents
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Hair coloring compositions which comprise: (A) non-nitrogenous chelating agents from the group consisting of polyphosphate; phosphonates; hydroxycarboxylates; polyacrylates; zeolite; and mixtures thereof; (B) an oxidative dye primary intermediate; and (C) an oxidative dye coupler; (D) and water are described. The present invention also relates to a method for coloring hair which comprises contacting said hair with a hair coloring composition as described above.
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- C-Glycosylation of tri-O-benzyl-2-deoxy-D-glucose: Synthesis of naphthyl-substituted 3,6-dioxabicyclo[3.2.2]nonanes
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The syntheses of naphthol 7, naphthol 8, naphthol 11 and naphthol 12 are described, starting from juglone 13. C-Glycosylation of naphthol 8 with benzyl-protected glycosyl donor 10 using trimethylsilyl trifluoromethanesulfonate and silver perchlorate or boron trifluoride-diethyl ether affords rearranged product 36 in which the glycosyl donor has undergone an unusual 1,6-hydride shift. Use of the corresponding naphthol 12 as the glycosyl acceptor under the same conditions affords the expected C-glycoside 34. Use of the naphthol 7 and naphthol 11 affords predominantly rearranged products 35 and 37 respectively, albeit in much lower yield than the reactions using the corresponding bromonaphthols. The study described herein establishes that introduction of an acetyl group to C-3, as in C-glycosylnaphthoquinone 4, as required for conversion to analogues of medermycin 1 such as 3, necessitates that the C-glycosylation step be effected before regioselective introduction of the acetyl group.
- Brimble,Brenstrum
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p. 1612 - 1623
(2007/10/03)
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- Process for the two-stage oxidation dyeing of keratin fibers with a manganese complex or salt and a 4-substituted 1-naphthol, and dyeing kit
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A process for the two-stage oxidation dyeing of keratin fibers by applying to the keratin fibers: in a first stage, at least one composition A containing at least one manganese salt and/or a manganese complex, in a second stage, at least one composition B having a pH of greater than or equal to 6, and resulting from the extemporaneous mixing of at least one composition B1 containing at least one 4-substituted 1-naphthol and at least one composition B2 containing at least one oxidizing agent, and corresponding multi-compartment dyeing kit.
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- Synthesis of defucogilvocarcin V isosteres via MAD-mediated conjugate addition of carbanions to naphthoquinone ketals
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Treatment of a complex between naphthoquinone ketal 7 and methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide (MAD) with aryllithium reagents prepared by metallation of oxazoline 13 and amide 18, gave conjugate adducts which were converted to defucogilvocarcin V analogs 2 and 3 via a short reaction sequence. Some problems encountered in the metallation of oxazoline 19, a structural analog of amide 18, are also described.
- Hart, David J.,Mannino, Anthony
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p. 3841 - 3856
(2007/10/03)
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- A New Synthesis of Defucogilvocarcin M
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A convergent synthesis of the title compound is described.The synthesis revolves around a MAD-mediated coupling of oxazoline 11 and naphthoquinone ketal 16 and requires eight steps via the longest linear sequence.
- Hart, David J.,Merriman, Gregory H.
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p. 5093 - 5096
(2007/10/02)
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- Dimeric Naphthoquinones, IV1). - Synthesis of Biramentaceone, Mamegakinone and Rotundiquinone
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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
- Laatsch, Hartmut
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p. 1321 - 1347
(2007/10/02)
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