96502-90-8Relevant academic research and scientific papers
Indoloquinones, part 7. Total synthesis of the potent lipid peroxidation inhibitor carbazoquinocin C by an intramolecular palladium-catalyzed oxidative coupling of an anilino-1,4-benzoquinone
Kn?lker, Hans-Joachim,Fr?hner, Wolfgang,Reddy, Kethiri R.
, p. 557 - 564 (2002)
A highly efficient total synthesis of the potent lipid peroxidation inhibitor carbazoquinocin C is presented. The key-step is a palladium(II)-catalyzed oxidative cyclization of an anilino-1,4-benzoquinone to a carbazole-1,4-quinone which proceeds in up to 91% yield. Using this approach the natural product is obtained in four steps and 39% overall yield starting from aniline.
TREATMENT OR PREVENTION OF LEUKAEMIA
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Page/Page column 15-16, (2021/04/23)
The present invention provides compounds for use in the treatment or prevention of leukaemia which are based on a 2-amino-[1,1']-bipbenyl or corresponding carbazole scaffold, in particular, it provides the following compounds of formula (I), their stereoi
Hit to Leads with Cytotoxic Effect in Leukemic Cells: Total Synthesis Intermediates as a Molecule Treasure Chest
Bj?rsvik, Hans-René,Gjertsen, Bj?rn Tore,Elumalai, Vijayaragavan
, p. 862 - 870 (2020/05/05)
A previously designed and developed 12-step total synthesis that includes [1,1′-biphenyl]-2-amine and carbazole intermediates and that ultimately produces the carbazole alkaloid carbazomycin G was exploited as a screening compound library with the goal of
Carbazomycin G: Method Development and Total Synthesis
Elumalai, Vijayaragavan,Gambarotti, Cristian,Bj?rsvik, Hans-René
, p. 1984 - 1992 (2018/05/15)
A novel total synthesis leading to the carbazole alkaloid carbazomycin G was designed and developed. The outlined synthetic route is composed of twelve synthetic steps including the transformations of the initial simple substrate and intermediates. To rea
Synthesis of the ABH rings of ecteinascidin 597 using a connective Pummerer-type cyclisation
Smith, Laura H. S.,Nguyen, Trung Thanh,Sneddon, Helen F.,Procter, David J.
supporting information; experimental part, p. 10821 - 10823 (2011/11/05)
A connective Pummerer-type cyclisation involving a cysteine derivative and an N-benzyl glyoxamide 3 has been applied in an asymmetric synthesis of the protected ABH rings 2 of the antitumour and antimicrobial natural product ecteinascidin 597.
New Drug Delivery System for Crossing the Blood Brain Barrier
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Page/Page column 25, (2008/06/13)
New ubiquinol analogs are disclosed, as well as methods of using these compounds to deliver drug moieties to the body.
Efficient and green telescoped process to 2-methoxy-3-methyl-[1,4] benzoquinone
Rodriguez Gonzalez, Raquel,Gambarotti, Cristian,Liguori, Lucia,Bjorsvik, Hans-Rene
, p. 1703 - 1706 (2007/10/03)
A telescoped process for the preparation of 2-methoxy-3-methyl-[1,4] benzoquinone is disclosed. When this novel process is compared to the prevailing method that utilizes Na2Cr2O7 as the oxidant, the novel process represen
Synthesis of methoxy-substituted phenols by peracid oxidation of the aromatic ring
Bjorsvik, Hans-Rene,Occhipinti, Giovanni,Gambarotti, Cristian,Cerasino, Leonardo,Jensen, Vidar R.
, p. 7290 - 7296 (2007/10/03)
A novel benign protocol for the preparation of hydroxy-methoxybenzene derivatives is disclosed. By utilizing this protocol, activated aromatic compounds such as l,3-dimethoxy-2-methyl-benzene and 1-(2,6-dimethoxyphenyl) ethanone are smoothly converted to the corresponding monohydroxylated compound. The reaction can be considered to be a normal aromatic electrophilic substitution reaction, and the regioselectivity for the reaction thus follows the similar rules as for electrophilic substitutions. The protocol is composed by benign reagents, namely, hydogenperoxide, acetic acid, and p-toluene sulfonic acid, which lead to the production of ethaneperoxoic acid in situ. The ethaneperoxoic acid operates as the hydroxylating reagent. The hydroxylation reaction is completed within a short period and requires moreover only mild experimental conditions, which make this novel protocol a green, cheap, and rapid process leading to hydroxy-methoxybenzene derivatives. The proposed reaction mechanism is supported by density functional theory and NMR spectroscopy experiments. The mechanism is constituted by two discrete steps: (a) addition of OH+ to the most nucleophilic carbon atom of the aromatic ring, which is the rate-determining step, and (b) the loss of the proton from the aromatic ring.
Access to orthogonal protected phenols - Synthesis of a silylated quinol
Siddiqi, Shahzad A.,Heckrodt, Thilo J.
, p. 328 - 331 (2007/10/03)
Herein we describe the synthesis of t-butyldimethylsilyl protected quinol (9), using an oxidation/reduction sequence to create the desired orthogonality. The title compound acts as a synthetic equivalent for a quinone, required in the total synthesis of E
Synthesis of a Diels-Alder precursor for the Elisabethin A skeleton
Heckrodt, Thilo J.,Mulzer, Johann
, p. 1857 - 1866 (2007/10/03)
A synthesis of a precursor 2 for the Elisabethin A skeleton is reported. Containing a masked quinone and a (E,Z)-diene sub-unit, it has the required elements for the envisaged intramolecular Diels-Alder reaction to form the tricyclic system of Elisabethin A. Starting from methylresorcinol, the sequence involves the preparation of an arylacetic acid, which was α-alkylated by a chiral building block. Subsequent HWE reaction and cis-selective Wittig olefination furnished the diene with the desired geometry.
