- Synthesis of Vitisins A and D Enabled by a Persistent Radical Equilibrium
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The first total synthesis of the resveratrol tetramers vitisin A and vitisin D is reported. Electrochemical generation and selective dimerization of persistent radicals is followed by thermal isomerization of the symmetric C8b-C8c dimer to the C3c-C8b isomer, providing rapid entry into the vitisin core. Computational results suggest that this synthetic approach mimics Nature's strategy for constructing these complex molecules. Sequential acid-mediated rearrangements consistent with the proposed biogenesis of these compounds afford vitisin A and vitisin D. The rapid synthesis of these complex molecules will enable further study of their pharmacological potential.
- Romero, Kevin J.,Keylor, Mitchell H.,Griesser, Markus,Zhu, Xu,Strobel, Ethan J.,Pratt, Derek A.,Stephenson, Corey R.J.
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Read Online
- Cu-Catalyzed: O -alkylation of phenol derivatives with alkylsilyl peroxides
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A Cu-catalyzed O-alkylation of phenol derivatives using alkylsilyl peroxides as alkyl radical precursors is described. The reaction proceeds smoothly under mild reaction conditions and the use of two different ligands with a Cu catalyst provides a wide range of products. A mechanistic study suggested that the reaction proceeds via a radical mechanism. This journal is
- Sakurai, Shunya,Kano, Taichi,Maruoka, Keiji
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supporting information
p. 81 - 84
(2021/01/14)
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- Visible light-induced mono-bromination of arenes with BrCCl3
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A highly efficient and regioselective bromination of electron-rich arenes and heteroarenes using commercially available BrCCl3as a “Br” source has been developed. The reaction was performed in air under mild conditions with photocatalyst Ru(bpy)3Cl2·6H2O, avoiding the usage of strong acids and strong oxidants. Mono-brominated products were obtained with medium to excellent yields (up to 94%). This strategy has shown good compatibility and highpara-selectivity, which will facilitate the complicated synthesis.
- Fan, Jiali,Wei, Qiancheng,Zhu, Ershu,Gao, Jing,Cheng, Xiamin,Lu, Yongna,Loh, Teck-Peng
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supporting information
p. 5977 - 5980
(2021/06/18)
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- Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
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Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.
- Mills, L. Reginald,Graham, Joshua M.,Patel, Purvish,Rousseaux, Sophie A. L.
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supporting information
p. 19257 - 19262
(2019/12/02)
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- Environmentally benign indole-catalyzed position-selective halogenation of thioarenes and other aromatics
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Halogenated aromatic compounds are the cores of many pharmaceutical, agricultural and chemical products but they are commonly prepared using electrophilic halogenation reactions in non-green chlorinated solvents under harsh conditions. A separate problem happens in the aromatic halogenation of thioarenes because they readily undergo oxidative side-reactions. Herein we report an environmentally benign electrophilic bromination of aromatics using an indole-catalytic protocol, which is suitable for a wide range of substrates including thioarenes.
- Shi, Yao,Ke, Zhihai,Yeung, Ying-Yeung
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supporting information
p. 4448 - 4452
(2018/10/17)
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- Zwitterionic-Salt-Catalyzed Site-Selective Monobromination of Arenes
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A zwitterionic-salt-catalyzed electrophilic monobromination of arenes with high regioselectivity has been developed. Under mild reaction conditions, a wide range of monobrominated aromatic compounds can be obtained in excellent yields. The reaction can be operated using an extremely low catalyst loading (0.05 mol %) with the inexpensive brominating agent N-bromosuccinimide. The versatility of this catalytic protocol has been demonstrated by the scale-up reaction with a 0.01 mol % catalyst loading to provide the selectively halogenated compound in quantitative yield.
- Xiong, Xiaodong,Tan, Fei,Yeung, Ying-Yeung
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supporting information
p. 4243 - 4246
(2017/08/23)
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- IMPROVED MODULATORS OF HEC1 ACTIVITY AND METHODS THEREFOR
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Compounds, compositions, and methods for modulation of Hec1/Nek2 interaction are provided. Such compounds disrupt Nek2/Hec1 binding and may be useful as chemotherapeutic agents for neoplastic diseases
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Paragraph 00151
(2013/06/27)
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- Design, syntheses, and characterization of pharmacophore based chemokine receptor CCR5 antagonists as anti prostate cancer agents
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Accumulating evidence has shown multiple roles that chemokine receptor CCR5 may play to promote the progression of several types of cancer. The mechanism of such promotion is believed to involve chronic inflammation that creates a microenvironment which e
- Arnatt, Christopher K.,Zaidi, Saheem A.,Zhang, Zhu,Li, Guo,Richardson, Amanda C.,Ware, Joy L.,Zhang, Yan
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p. 647 - 658
(2013/10/22)
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- Analogues of fenarimol are potent inhibitors of trypanosoma cruzi and are efficacious in a murine model of chagas disease
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We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC50s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.
- Keenan, Martine,Abbott, Michael J.,Alexander, Paul W.,Armstrong, Tanya,Best, Wayne M.,Berven, Bradley,Botero, Adriana,Chaplin, Jason H.,Charman, Susan A.,Chatelain, Eric,Von Geldern, Thomas W.,Kerfoot, Maria,Khong, Andrea,Nguyen, Tien,McManus, Joshua D.,Morizzi, Julia,Ryan, Eileen,Scandale, Ivan,Thompson, R. Andrew,Wang, Sen Z.,White, Karen L.
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supporting information; experimental part
p. 4189 - 4204
(2012/07/27)
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- Synthesis of 1,4-bis[2,2-bis(4-alkoxyphenyl)vinyl]benzenes and side chain modulation of their solid-state emission
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Figure Presented. A series of 1,4-bis[2,2-bis(4-alkoxyphenyl)vinyl]benzene molecules with aggregation-induced emission (AIE) activity were synthesized. The conformations and packing arrangements of these molecules in the solid state can be adjusted by changing the side chains, which subsequently modulates their solid-state emission. The fluorescence quantum yield of 1e with the n-C 6H13 side chain in the solid state could reach up to 60.3% in the solid state.
- An, Peng,Shi, Zi-Fa,Dou, Wei,Cao, Xiao-Ping,Zhang, Hao-Li
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supporting information; experimental part
p. 4364 - 4367
(2010/11/17)
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- 4,5-DIHYDRO-OXAZOL-2-YL AMINE DERIVATIVES
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The present invention relates to a compounds of formula I wherein R1, R1′, R2, R3, R4, X, Ar, and m are as defined in the specification and claims and pharmaceutically active acid addition salts thereof. Compounds of the invention have Asp2 (β-secretase, BACE 1 or Memapsin-2) inhibitory activity and are useful for the treatment of diseases characterized by elevated β-amyloid levels or β-amyloid deposits, particularly Alzheimer's disease.
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Page/Page column 21
(2009/09/05)
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- Asymmetric synthesis of (+)- and (-)-latifine
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A concise and novel synthesis of isoquinoline alkaloids (S)-latifine and of its antipode is reported. The key step relies on the stereoselective reduction of an appropriately substituted diarylenamine equipped with a chiral auxiliary followed by Pictet-Sp
- Couture, Axel,Deniau, Eric,Grandclaudon, Pierre,Lebrun, Stephane
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p. 1309 - 1316
(2007/10/03)
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- Carboxy-substituted cinnamides: A novel series of potent, orally active LTB4 receptor antagonists
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A series of carboxy-substituted cinnamides were investigated as antagonists of the human cell surface leukotriene B4 (LTB4) receptor. Binding was determined through measurement of [3H]-LTB4 displacement from hum
- Greenspan, Paul D.,Fujimoto, Roger A.,Marshall, Paul J.,Raychaudhuri, Anil,Lipson, Kenneth E.,Zhou, Huanghai,Doti, Robert A.,Coppa, David E.,Zhu, Lijuan,Pelletier, Roberta,Uziel-Fusi, Susan,Jackson, Robert H.,Chin, Michael H.,Kotyuk, Bernard L.,Fitt, John J.
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p. 164 - 172
(2007/10/03)
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- Cyanine Borate Salts That Form Penetrated Ion Pairs in Benzene Solution: Synthesis, Properties, and Structure
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A series of cyanine borate salts were prepared and studied by laser spectroscopy, fluorescence spectroscopy, NMR spectral methods, and computer modeling.Analysis of the chemical, physical, and spectral properties of these salts shows that, in benzene solution, they form penetrated ion pairs.The center-to-center distance between the ions is less than the sum of the individual ionic radii.We call such structures penetrated ion pairs.Penetration affects the properties of the cyanine dyes in unique ways that are described.
- Murphy, Sean,Yang, Xiquiang,Schuster, Gary B.
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p. 2411 - 2422
(2007/10/02)
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- Evidence for the Occurrence of Substitution Side Products in Grignard Reactions
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In the formation of Grignard reagents from 4-bromoalkoxybenzene and their subsequent coupling reactions with allylic halides, the unusual minor side products, 8 - 14 have been obtained.
- Lajis, Nordin Hj.,Khan, Mohammad Niyaz,Hassan, Hazimah A.
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p. 3405 - 3410
(2007/10/02)
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