- Total synthesis of (±)-antroquinonol D
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Total synthesis of (±)-antroquinonol D, which is isolated from very expensive and rarely found Antrodia camphorata and which has potential anticancer properties, was achieved from 4-methoxyphenol. In addition, a Michael addition to dimethoxy cyclohexadien
- Sulake, Rohidas S.,Jiang, Yan-Feng,Lin, Hsiao-Han,Chen, Chinpiao
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- Catalytic Enantioselective Diels-Alder Reactions of 1,4-Quinone Monoketals
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matrix presented Achiral 1,4-quinone monoketals function well as dienophiles in enantioselective Diels-Alder reactions catalyzed by a chiral Ti(IV) Lewis acid.
- Breuning, Matthias,Corey
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- Thermal and Photochemical Rearrangements of Cyclopropyl Ethers of p-Quinols. Competing Reaction Pathways Leading to Five- and Six-Membered Ring Spirocyclic Ketones
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Cyclopropyl ethers of p-quinols were prepared by reaction of 3''-methylenedispirocyclohexadiene-4',1''(3''H)-isobenzofuran> and the associated ketone with ethyl diazoacetate/rhodium(II) acetate and diethylzinc/methylene iodide, re
- Biggs, Timothy N.,Swenton, John S.
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- Ring-fused compound, pharmaceutical composition containing same and application of compound
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The invention discloses a ring-fused compound, a preparation method thereof, pharmaceutical composition containing the compound and an application of the compound. A polycyclic compound (I) as well asan isomer, a prodrug, a stable isotopic derivative or pharmacologically acceptable salt of the compound (I) has the following structure. The polycyclic compound has good IDO1 and/or TDO2 inhibition functions, can effectively treat, relieve and/or prevent various diseases which are related with IDO1 and/or TDO2, such as cancer, virus infection, autoimmune diseases or the like.
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Paragraph 0287-0289
(2018/04/01)
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- Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N′-dimethylhydrazine dihydrochloride
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An unexpected nucleophilic chlorination of a quinone monoketal while carrying out a pyrazolidine synthesis has led to a general preparation of multisubstituted phenols. The products are obtained in good to high yields under mild conditions. The bridged pyrazolidines that were the original targets are obtained in the presence of a protic solvent. This journal is the Partner Organisations 2014.
- Yin, Zhiwei,Zhang, Jinzhu,Wu, Jing,Green, Riana,Li, Sihan,Zheng, Shengping
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supporting information
p. 2854 - 2858
(2014/05/06)
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- Total synthesis and structural confirmation of (±)-cuevaene A
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The total synthesis and structural reassignment of cuevaene A have been completed. The key synthetic steps in the total synthesis included a base-promoted double conjugate addition and further elaboration to generate the tricyclic core structure, followed by construction of the trienoic acid side chain. Detailed comparison of proton and carbon NMR data with published values enabled the connectivity of the natural product, which had been debated in earlier publications, to be confirmed.
- Craven, Philip G.E.,Taylor, Richard J.K.
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supporting information
p. 5422 - 5425
(2012/10/30)
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- A total synthesis of millingtonine a
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A total synthesis of millingtonine A, a diglycosylated alkaloid, has been accomplished. Millingtonine A possesses a unique racemic tricyclic core structure not known from any other natural or synthetic source until now. The synthesis features a key bond-f
- Wegner, Jens,Ley, Steven V.,Kirschning, Andreas,Hansen, Anne-Lene,Montenegro Garcia, Javier,Baxendale, Ian R.
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supporting information; experimental part
p. 696 - 699
(2012/04/17)
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- Method for the Production of Substituted and Unsubstituted Cyclohexanone Monoketals
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The invention relates to a novel process for preparing and isolating known substituted and unsubstituted 1,4-cyclohexanone monoketals.
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Page/Page column 4
(2010/09/05)
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- An efficient protocol for the enantioselective preparation of a key polyfunctionalized cyclohexane. New access to (R)- and (S)-4-hydroxy-2- cyclohexenone and (R)- and (S)-trans-cyclohex-2-ene-1,4-diol
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(Chemical Equation Presented) Starting from very accessible raw materials such as p-methoxyphenol, ethylene glycol, and thiophenol, a protocol has been developed to prepare multigram quantities of the polyfunctionalized cyclohexane (±)-7. A highly efficie
- Bayon, Pau,Marjanet, Georgina,Toribio, Gladis,Alibes, Ramon,De March, Pere,Figueredo, Marta,Font, Josep
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p. 3486 - 3491
(2008/09/21)
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- Synthesis of both enantiomers of conduritol C tetraacetate and of meso-conduritol D tetraacetate by oxidation of benzoquinone bis(ethylene acetal)
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Epoxidation of p-benzoquinone bis(ethylene acetal) (1) with m-chloroperbenzoic acid or hydrogen peroxide/benzonitrile afforded corresponding monoepoxide 2, which was converted into p-benzoquinone mono(ethylene acetal) monoepoxide 5 with perchloric acid. D
- Lang, Martin,Ziegler, Thomas
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p. 768 - 776
(2008/02/07)
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- New cyclohexadienone derivatives: Preparation and chiral discrimination in high-pressure diels - Alder cycloadditions
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A wide range of cyclohexadienones has been synthesised in order to study their reactivity and their regio- and stereoselectivity with the enantiopure diene 1 under high-pressure conditions. Computational investigations were used to point out some paramete
- Tran-Huu-Dau, Marie-Elise,Wartchow, Rudolf,Winterfeldt, Ekkehard,Wong, Yung-Sing
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p. 2349 - 2369
(2007/10/03)
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- Photochemical rearrangements of quinone monoketals
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We have studied the photochemistry of over 15 quinone cyclic monoketals, which were prepared by diol exchange from the dimethyl ketals, Swanton oxidation/hydrolysis, or direct ketalization. Their reactions in acidic media are generally explained by the classical mechanism for cyclohexadienone photochemical (di-π-methane) rearrangements: photocyclization to a cyclopropane-oxyallylcation that is protonated, followed by sovolysis. This reaction pathway provides, after hydrolysis, β-carboxy-substituted cyclopentenones. With a substituent at the β-position of the quinone monoketal, rearrangement selectivity is modestly in favor of the more substituted alkene product. With a substituent at the α-position of the quinone monoketal, rearrangement selectivity is strongly in favor of the less substituted alkene product. Possible mechanistic reasoning to explain these observations is offered.
- Pirrung, Michael C.,Nunn, David S.
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p. 5707 - 5738
(2007/10/03)
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- Chiral synthesis of (+)-8′-demethyl abscisic acid
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An enantioselective synthesis of (+)-8′-demethyl ABA (2) is described. The chiral intermediate 7 was prepared by yeast reduction of a substituted monoprotected cyclohexa-2,5-dien-1,4-dione (9) synthesized through a phenol oxidation. The scope and limitations of the phenol oxidation is described. 8′-Demethyl ABA shows ABA-like activity in wheat embryo germination inhibition, showing that the 8′-methyl group is not essential for biological activity.
- Rose, Patricia A.,Lei, Bo,Shaw, Angela C.,Walker-Simmons,Napper, Scott,Quail, J. Wilson,Abrams, Suzanne R.
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p. 1836 - 1843
(2007/10/03)
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- An efficient, simple and inexpensive method for the preparation of 1,4-benzoquinone monoketals via anodic oxidation of 1,4-dimethoxybenzenes
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Anodic oxidation of a series of 1-substituted-2,5-dimethoxybenzenes gives 2-substituted-1,1,4,4-tetramethoxycyclohexa-2,5-dienes in almost quantitative crude yield. Selective monohydrolysis of these bis-ketals is possible in many cases, and gives 3-substi
- Gautier,Lewis,McKillop,Taylor
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p. 2989 - 3008
(2007/10/02)
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- PHOTOCHEMICAL REARRANGEMENTS OF QUINONE MONOKETALS. SYNTHESIS OF SUBSTITUTED CYCLOPENTENONES
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The irradiation of quinone ethylene monoketals in acetic acid leads in high yield to substituted 4-(alkoxycarbonyl)cyclopentenones.
- Pirrung, Michael C.,Nunn, David S.
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p. 163 - 166
(2007/10/02)
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- A Mechanistic Study of the Thermal Disproportionation Reaction of Quinone Monoketals
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Thermolysis of quinone monoketals 1a-d at 180 deg C leads to disproportionation to the p-alkoxyphenols 2a-d and the carbonyl compounds derived from the alcohol moiety of the ketal.The thermolysis of 4,4-dimethoxy-2,5-cyclohexadienone (1a) followed first-order kinetics, and the rate of reaction decreased by a factor of 3.6 when the methoxy groups were replaced with methoxy-d3 groups.The suggested mechanism for the reaction involves reversible dissociation of 1a into a p-methoxyphenoxy-methoxy radical pair, followed by rate-controlling hydrogen atom transfer to give p-methoxyphenol and formaldehyde.Although 1a has a half-life of about 4 h at 180 deg C, the monoethylene glycol ketal of benzoquinone was recovered in > 90percent yield after heating for 24 h at the same temperature.Finally, acid-catalysed exchange of 3,3,6,6-tetramethoxy-1,4-cyclohexadiene with alcohols furnished a convenient route to quinone bisketals not obtainable in good yield via anodic oxidation.
- Capparelli, Michael P.,Swenton, John S.
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p. 5360 - 5364
(2007/10/02)
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- Spirodienones. Part 5. The Synthesis and Reactions of N-Sulphonylcyclohexadienimines
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The anodic or chemical oxidation of para-substituted sulphonanilides gives 4,4-disubstituted N-sulphonylcyclohexadienimines, which, from appropriately substituted anilines, may be spirocyclic.The scope and limitations of the synthesis are described, and mechanism proposed.The selective hydrolysis of the dienimines to the corresponding dienones provides a convenient route to the latter compounds.The reaction of some of the dienimines with dienes is discussed.
- Coutts, Ian G. C.,Culbert, Nicholas J.,Edwards, Mark,Hadfield, John A.,Musto, Donald R.,et al.
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p. 1829 - 1836
(2007/10/02)
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- SPIRODIENONES IV THE SYNTHESIS OF N-SULPHONYLCYCLOHEXADIENIMINES AND RELATED DIENONES
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Oxidation of N-4-toluenesulphonylanilines bearing appropriate para substituents gives good yields of spirocyclic N-sulphonylcyclohexadienimines; these compounds may be selectively hydrolysed to the corresponding spirodienones.
- Coutts, Ian G. C.,Edwards, Mark,Musto, Donald R.,Richards, David J.
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p. 5055 - 5056
(2007/10/02)
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