Royal Society of Chemistry

Studies on copper(I)-catalyzed highly regio- and stereo-selective hydroboration of alkynamides

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5945-5953
DOI: 10.1039/C4OB00979G, PaperGuangke He, Shan Chen, Qiang Wang, Hai Huang, Qijun Zhang, Dongming Zhang, Rong Zhang, Hongjun Zhu
The regio-selectivity of the Cu(I)-catalyzed hydroboration of N-(1-alkynyl)amides is unexpectedly opposite to that in the carbometallation reaction of alkynamides.
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Structurally modified natural sesquiterpene lactones constitute effective and less toxic schistosomicidal compounds

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00426D, PaperDaiane Cristina Sass, Gustavo Oliveira Morais, Ricardo Augusto Crema Miranda, Lizandra Guidi Magalhaes, Wilson Roberto Cunha, Raquel Alves dos Santos, Nilton Syogo Arakawa, Fernando Batista Da Costa, Mauricio Gomes Constantino, Vladimir Constantino Gomes Heleno
Selective obtention of novel natural sesquiterpene lactone derivatives with interesting schistosomicidal activity and low toxicity, together with complete NMR assignments.
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Solid-phase synthesis of peptoid-like oligomers containing diverse diketopiperazine units

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5831-5834
DOI: 10.1039/C4OB00829D, CommunicationSujit Suwal, Thomas Kodadek
An efficient protocol for the solid-phase synthesis of diverse diketopiperazines is reported.
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An acridinium-based sensor as a fluorescent photoinduced electron transfer probe for proton detection modulated by anionic micelles

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00559G, PaperStefano Basili, Tiziana Del Giacco, Fausto Elisei, Raimondo Germani
Photoinduced electron transfer has been demonstrated to be the quenching mechanism for the fluorescent pH sensor based on the 9-amino-10-methylacridinium chromophore. The presence of anionic micelles causes a significant increase in the detection sensitivity of pH.
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Synthesis and evaluation of antineurotoxicity properties of an amyloid-[small beta] peptide targeting ligand containing a triamino acid

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00959B, PaperDmytro Honcharenko, Partha Pratim Bose, Jyotirmoy Maity, Firoz Roshan Kurudenkandy, Alok Juneja, Erik Floistrup, Henrik Biverstal, Jan Johansson, Lennart Nilsson, Andre Fisahn, Roger Stromberg
A new triamino acid enables synthesis of an amyloid-[small beta] peptide (A[small beta]) targeting ligand with additional A[small beta]-ligand interactions that gives protection towards A[small beta]-induced reduction of gamma oscillations in hippocampal slice preparation.
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Convenient access to readily soluble symmetrical dialkyl-substituted [small alpha]-oligofurans

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00898G, PaperEdward E. Korshin, Gregory M. Leitus, Michael Bendikov
A combination of heteroatom directed lithiation/CuCl2-induced homocoupling, Wittig olefination/Pd-catalyzed transfer hydrogenation followed by Suzuki-Miyaura or Stille cross-coupling enables convenient access to dialkyl-substituted [small alpha]-oligofurans of potential interest for organic electronics.
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Synthesis of methyl 2-cyano-3,12-dioxo-18[small beta]-olean-1,9(11)-dien-30-oate analogues to determine the active groups for inhibiting cell growth and inducing apoptosis in leukemia cells

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00703D, PaperXiaojing Li, Yuetong Wang, Yuan Gao, Lei Li, Xin Guo, Dan Liu, Yongkui Jing, Linxiang Zhao
A series of CDODO-Me-12 analogues were synthesized with improved ability to inhibit cell growth and induce apoptosis in HL-60 cells.
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Desilylative activation of TMSCN in chemoselective Strecker-Ugi type reaction: functional fused imidazoles as building blocks as an entry route to annulated purines

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00882K, PaperSankar K. Guchhait, Vikas Chaudhary
Nucleophilic activation of TMSCN as an isocyanide equivalent by DABCO-THF in the Strecker-Ugi reaction facilitates the synthesis of functional imidazoles which, as building blocks, afford access to C8-N9 annulated purines.
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Mutation of Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase at Trp-110 affects stereoselectivity of aromatic ketone reduction

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5905-5910
DOI: 10.1039/C4OB00794H, PaperJay M. Patel, Musa M. Musa, Luis Rodriguez, Dewey A. Sutton, Vladimir V. Popik, Robert S. Phillips
Secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus was mutated at Trp-110, and mutant enzymes with high activity and high stereoselectivity for aromatic ketone reduction were identified.
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Breaking the dichotomy of reactivity vs. chemoselectivity in catalytic SN1 reactions of alcohols

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5990-5994
DOI: 10.1039/C4OB01265H, PaperMalik Hellal, Florian C. Falk, Elena Wolf, Marian Dryzhakov, Joseph Moran
B(C6F5)3 possesses a different reactivity/chemoselectivity profile than traditional Lewis and Bronsted acids and is effective at enabling catalytic SN1 reactions of alcohols in the presence of acid sensitive groups without compromising reaction rates, substrate scope or catalyst loadings.
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Enantioselective palladium catalyzed conjugate additions of ortho-substituted arylboronic acids to [small beta],[small beta]-disubstituted cyclic enones: total synthesis of herbertenediol, enokipodin A and enokipodin B

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5883-5890
DOI: 10.1039/C4OB01085J, PaperJeffrey Buter, Renee Moezelaar, Adriaan J. Minnaard
Palladium catalyzed asymmetric conjugate addition of ortho-substituted arylboronic acids to cyclic enones and its application in natural product synthesis.
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Design, synthesis and biological evaluation of hydrogen sulfide releasing derivatives of 3-n-butylphthalide as potential antiplatelet and antithrombotic agents

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5995-6004
DOI: 10.1039/C4OB00830H, PaperXiaoli Wang, Linna Wang, Xiao Sheng, Zhangjian Huang, Tingting Li, Ming Zhang, Jinyi Xu, Hui Ji, Jian Yin, Yihua Zhang
Compound 8e protected against the collagen and adrenaline induced thrombosis in mice, and exhibited greater antithrombotic activity than NBP and aspirin in rats.
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C 3-Symmetric chiral trisimidazoline-catalyzed Friedel-Crafts (FC)-type reaction

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5827-5830
DOI: 10.1039/C4OB00925H, CommunicationShinobu Takizawa, Shuichi Hirata, Kenichi Murai, Hiromichi Fujioka, Hiroaki Sasai
The first imidazoline-catalyzed enantioselective Friedel-Crafts (FC)-type reaction was established using C3-symmetric chiral trisimidazolines.
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Efficient asymmetric synthesis of N-protected-[small beta]-aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01047G, PaperRajesh Malhotra, Tushar K. Dey, Swarup Dutta, Sourav Basu, Saumen Hajra
First regioselective ring opening of serine derived cyclic sulfamidate with ArONa is developed to provide an easy and direct access of a variety of N-Boc- and N-PMB protected [small beta]-aryloxy-[small alpha]-amino acids with complete retention of enantiopurity in moderate to high yields.
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Mercaptobenzoic acid-palladium(0) complexes as active catalysts for S-benzylation with benzylic alcohols via ([small eta]3-benzyl)palladium(II) cations in water

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5964-5972
DOI: 10.1039/C4OB00688G, PaperHidemasa Hikawa, Isao Azumaya
Mercaptobenzoic acid-palladium(0) complexes show high catalytic activity for S-benzylation with benzylic alcohols via the ([small eta]3-benzyl)palladium(II) cation in water. The catalytic system can be performed using only 2.5 mol% Pd2(dba)3 without the phosphine ligand or other additives.
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Palladium-catalyzed synthesis of isoindoloquinazolinones via dicarbonylation of 1,2-dibromoarenes

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5835-5838
DOI: 10.1039/C4OB01103A, CommunicationJianbin Chen, Helfried Neumann, Matthias Beller, Xiao-Feng Wu
The first example of palladium-catalyzed carbonylative synthesis of isoindoloquinazolinones has been developed. Using 1,2-dibromobenzenes and 2-aminobenzyl amine as substrates, the products were isolated in moderate to good yields with the installation of two molecules of CO.
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Copper catalyzed C-O bond formation via oxidative cross-coupling reaction of aldehydes and ethers

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00862F, CommunicationQuan Wang, Hao Zheng, Wen Chai, Dianyu Chen, Xiaojun Zeng, Renzhong Fu, Rongxin Yuan
A practical and efficient construction of C-O bonds via oxidative cross-coupling reaction of aldehydes and ethers has been realized under open air. When 2 mol% copper was used as the catalyst, various [small alpha]-acyloxy ethers were obtained with up to 93% isolated yield.
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Pyridine-phosphinimine ligand-accelerated Cu(I)-catalyzed azide-alkyne cycloaddition for preparation of 1-(pyridin-2-yl)-1,2,3-triazole derivatives

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5954-5963
DOI: 10.1039/C4OB01176G, PaperRanfeng Sun, Huangdong Wang, Jianfeng Hu, Jiudong Zhao, Hao Zhang
A new phosphinimine ligand was used in the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction of tetrazolo[1,5-a]pyridines (not active in traditional CuAAC reactions) and alkynes for the first time and a series of 1-(pyridin-2-yl)-1,2,3-triazole derivatives were prepared.
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Monitoring and inhibition of Plk1: amphiphilic porphyrin conjugated Plk1 specific peptides for its imaging and anti-tumor function

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5876-5882
DOI: 10.1039/C4OB00853G, PaperHongguang Li, Chi-Fai Chan, Wai-Lun Chan, Sam Lear, Steven L. Cobb, Nai-Ki Mak, Terrence Chi-Kong Lau, Rongfeng Lan, Wai-Kwok Wong, Ka-Leung Wong
Polo-like kinase 1 (Plk1) is well-known for taking part in cell cycle progression and regulation.
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One-pot synthesis of polysubstituted 3-acylpyrroles by cooperative catalysis

Org. and Biomol. Chem. - 21 July, 2014 - 09:17

Org. Biomol. Chem., 2014, 12,5822-5826
DOI: 10.1039/C4OB01019A, CommunicationHai-Lei Cui, Fujie Tanaka
Polysubstituted 3-acylpyrroles were synthesized from readily available unsaturated ketones and N-substituted propargylated amines via an aza-Michael/alkyne carbocyclization cascade followed by oxidation in one pot.
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