Org. and Biomol. Chem.

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1,1-Alkenylboration of diarylphosphino-enynes: convenient synthetic entry to vicinal P/B Lewis pairs at extended conjugated [small pi]-frameworks

1 November, 2014 - 11:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02134G, PaperGerald Kehr, G Erker, Constantin Gabriel Daniliuc, Guo-Qiang Chen
Alkenylboranes R-CH=CH-B(C6F5)2 undergo carbon-carbon coupling by means of 1,1-alkenylboration with diarylphosphino-enynes to give substituted conjugated hexatriene derivatives that bear a vicinal pair of B(C6F5)2 Lewis acid and PAr2 Lewis base...
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Development of a novel fluorescence probe capable of assessing the cytoplasmic entry of siderophore-based conjugates

30 October, 2014 - 10:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01810A, CommunicationHyeon Seok Kim, Woon Young Song, Hak Joong Kim
A novel fluorescence probe capable of assessing the cytoplasmic entry of siderophore-based conjugates was synthesized and evaluated by photochemical characterization and cell-based assays. The specific responsiveness to the cytoplasmic entry...
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Amino acid-linked porphyrin-nitroimidazole antibiotics targeting Porphyromonas gingivalis

30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01841A, PaperSimon A. Dingsdag, Benjamin C-M. Yap, Neil Hunter, Maxwell J. Crossley
Amino acid-linked porphyrin-nitroimidazole adducts, as potent as metronidazole, are highly selective for Porphyromonas gingivalis.
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Late-Stage Diversification of Biologically Active Pyridazinones via Direct C-H Functionalization Strategy

30 October, 2014 - 10:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02061H, PaperWei Li, Zhoulong Fan, Kaijun Geng, Youjun Xu, Ao Zhang
Divergent C-H functionalization reactions (arylation, carboxylation, olefination, thiolation, acetoxylation, halogenation, naphthylation) using a pyridazinone moiety as an internal directing group were successfully established. This approach offers a late-stage, ortho-selective diversification...
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Sc(OTf)3-mediated 1,3-dipolar cycloaddition-ring cleavage-rearrangement: a highly stereoselective access to Z-[small beta]-enaminonitriles

30 October, 2014 - 10:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01801J, PaperYing-chun Wang, Yu-Yang Xie, Xian-chun Tan, Hengshan Wang, Ying-ming Pan
A novel and highly stereoselective synthesis of Z-[small beta]-enaminonitriles from azides and [small alpha],[small beta]-unsaturated nitriles is reported. The reaction proceeds via a 1,3-dipolar cycloaddition-ring cleavage-rearrangement cascade mediated by catalytic amount of Sc(OTf)3....
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The synthesis of 3-hydroxy-2,4,8-trimethyldec-8-enolides and an approach to 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide

30 October, 2014 - 10:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01792G, PaperRosario Hern�ndez- Gal�n, Jose Manuel Botubol, Maria Jesus Duran-Pena, Antonio Jose Macias-Sanchez, I. G. Collado, James R Hanson
The synthesis of several derivatives of 3-hydroxy-2,4,8-trimethyldec-8-enolide and attempts at the synthesis of 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (1), a structure which has been assigned to a metabolite of the phytopathogenic fungus, Botrytis cinerea,...
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Ametantrone-based compounds as potential regulators of Tau pre-mRNA alternative splicing

30 October, 2014 - 10:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01925C, PaperGerard Artigas, Paula Lopez-Senin, Carlos Gonzalez, Nuria Escaja, Vicente Marchan
Tau pre-mRNA contains a stem-loop structure involved in the regulation of the alternative splicing of tau protein. We describe here a new family of Tau RNA ligands selected by a...
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Novel Synthesis of 5-methyl-5,10-dihydroindolo[3,2-b]indoles by Pd-catalyzed C-C and two-fold C-N coupling reactions

30 October, 2014 - 10:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01723D, PaperTran Quang Hung, Soren Hancker, Alexander Villinger, Stefan Lochbrunner, Tuan T Dang, Aleksey Friedrich, Wolfgang Breitsprecher, Peter Langer
A series of 5,10-dihydroindolo[3,2-b]indoles was successfully prepared by an efficient two-step strategy based on site-selective Pd-catalyzed cross-coupling reaction with N-methyl-2,3-dibromoindole and subsequent cyclization by two-fold Pd-catalyzed C-N coupling with amines....
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Asymmetric synthesis of axially chiral anilides by Pd-catalyzed allylic substitutions with P/olefin ligands

30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01087F, PaperYilin Liu, Xiangqing Feng, Haifeng Du
Palladium-catalyzed allylic substitutions of ortho-substituted anilides using P/olefin ligands were achieved to afford chiral anilides with up to 84% ee.
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Synthesis of fully functionalized aglycone of lycoperdinoside A and B

30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01716A, PaperBalla Chandrasekhar, Sudhakar Athe, P. Purushotham Reddy, Subhash Ghosh
Synthesis of fully functionalized aglycone of lycoperdinoside A and B is achieved via Pd-catalyzed Stille-Migita cross coupling and Evans syn- and anti aldol reactions as key steps.
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Pd-catalyzed oxidative C-H alkenylation for synthesizing arylvinyltriazole nucleosides

30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01836B, PaperJingjie Tang, Mei Cong, Yi Xia, Gilles Quelever, Yuting Fan, Fanqi Qu, Ling Peng
Pd-catalyzed oxidative C-H alkenylation: an effective method for synthesizing arylvinyltriazole nucleosides in good yields and with large functional group tolerance.
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Indium-Catalyzed Intramolecular Hydroarylation of Aryl Propargyl Ethers

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02033B, PaperLorena Alonso-Maranon, M. Montserrat Martinez, Luis Sarandeses, Jose Perez Sestelo
Indium(III) halides catalyze efficiently the intramolecular hydroarylation (IMHA) of aryl propargyl ethers. The reaction proceeds regioselectively with a variety of electron-rich and electron-deficient benzenes and with terminal and internal alkynes...
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Preparation of Cycloheptane Ring by Nucleophilic Cyclopropanation of 1,2-Diketones with Bis(iodozincio)methane

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01474J, PaperSeijiro Matsubara, Ryosuke Haraguchi, Yoshiaki Takada
We used a microflow system to study the nucleophilic cyclopropanation of hexa-1,5-diene-3,4-diones with bis(iodozincio)methane. This reaction afforded the zinc alkoxides of cis-dialkenylcylopropane-1,2-diols stereoselectively. The subsequent oxy-Cope rearrangement of cis-dialkenylcylopropane-1,2-diols afforded...
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Targeting DNA with small molecules: a comparative study of a library of azonia aromatic chromophores

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01465K, PaperJuan J. Vaquero, Rosa Suarez, Pedro Bosch, Dr. David Sucunza, Ana M. Cuadro, Alberto Domingo, Francisco Mendicuti
A library of azonia aromatic cations has been studied in order to gain an insight into the role of the size, shape and charge distribution on the fluorescence, DNA interactions...
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Irriversible Covalent Modification of Type I Dehydroquinase by a Stable Schiff Base

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01782J, PaperLorena Tizon, Maria Maneiro, Antonio Peon, Jose Otero, Emilio Lence, Sergio Poza, Mark J. van Raaij, Paul Thompson, Alastair R. Hawkins, Concepcion Gonzalez-Bello
The irreversible inhibition of type I dehydroquinase (DHQ1), the third enzyme of the shikimic acid pathway, has been investigated by structural, biochemical and computational studies. Two epoxides, which are mimetics...
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Improved synthesis of the super antioxidant, ergothioneine and its biosynthetic pathway intermediates.

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02023E, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Anwar Jardine, Peguy Lutete Khonde
Ergothioneine along with mycothiol, are low molecular mass redox protective thiols present in Actinomycetes, in particular mycobacteria. We report the improved chemical synthesis of ergothioneine (ESH) and biosynthetic pathway intermediates...
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Synthesis and Antifungal Activity of 1,2,3-Triazole Phenylhydrazone Derivatives

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01758G, PaperZhicheng Dai, Yongfei Chen, Mao Zhang, Shengkun Li, Tingting Yang, Li Shen, Jianxin Wang, Shao-Song Qian, Hai-Liang Zhu, Yonghao Ye
A series of 1,2,3-triazole phenylhydrazone were designed and synthesized as antifungal agents. Their structures were determined based on 1H-NMR spectroscopy, MS, elemental analysis and X-ray single-crystal diffraction. The antifungal activities...
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Chiral recognition with a benzofuran receptor which mimics an oxyanion hole

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01954G, PaperAngel L. Fuentes de Arriba, Angel Gomez Herrero, Omayra Hernandez Rubio, Laura Marcos Monleon, Luis Simon, Victoria Alcazar, Francisca Sanz, Joaquin Rodriguez Moran
A new chiral benzofuran receptor has been synthesized and its properties in the association of amino acid derivatives have been studied. X-ray structures were obtained and these corroborate the presence...
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Mixed non-covalent assemblies of ethynyl nile red and ethynyl pyrene along oligonucleotide templates

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01860E, PaperPhilipp Ensslen, Yannic Fritz, Hans-Achim Wagenknecht
Ethynyl pyrene and ethynyl nile red as modifications at the 5-position of 2'-deoxuridines self-assemble non-covalently and specifically along oligo-2'-deoxyadenosines as templates. Oligo-2'-deoxyadenosines of the lengths (dA)10 - (dA)20 are able...
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Efficient Merging of Copper and Photoredox Catalysis for the Asymmetric Cross-Dehydrogenative-Coupling of Alkynes and Tetrahydroisoquinolines

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02138J, PaperInna Perepichka, Soumen Kundu, Zoe Hearne, Chao-Jun Li
A highly efficient catalytic asymmetric alkynylation of prochiral CH2 groups in tetrahydroisoquinoline was developed using copper catalyzed cross-dehydrogenative-coupling of sp3 and sp C-H bonds with the assistance of a photocatalyst...
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