Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Dissecting non-covalent interactions in oxazaborolidinium catalyzed cycloadditions of maleimides

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1717-1720
DOI: 10.1039/C4OB00009A, CommunicationRobert S. Paton
Asymmetric induction in oxazaborolidinium-catalyzed cycloadditions of maleimides results from favourable dispersive interactions, and not non-classical hydrogen bonding.
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Synthesis of 3-acyltetramates by side chain manipulation and their antibacterial activity

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1711-1716
DOI: 10.1039/C4OB00095A, CommunicationSong Wei Benjamin Tan, Christina L. L. Chai, Mark G. Moloney
An efficient approach for the introduction of 3-acyl side chain groups onto a core tetramate system, which are suitable for further manipulation by nucleophilic displacement or Horner-Wadsworth-Emmons coupling, provides access to a diverse library of substituted tetramates related to two distinct classes of natural products, equisetin and pramanicin.
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Lead identification and structure-activity relationships of heteroarylpyrazole arylsulfonamides as allosteric CC-chemokine receptor 4 (CCR4) antagonists

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1779-1792
DOI: 10.1039/C3OB42443J, PaperAfjal H. Miah, Royston C. B. Copley, Daniel O'Flynn, Jonathan M. Percy, Panayiotis A. Procopiou
A combination of X-ray diffraction studies and SAR provided pyrazole 33 as a potent CCR4 antagonist with good physicochemical properties.
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Principles of modern solid-phase oligosaccharide synthesis

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1686-1698
DOI: 10.1039/C3OB42343C, Review ArticleClay S. Bennett
This perspective describes principles of modern solid-phase oligosaccharide synthesis, including technologies for automation and areas where further work is needed.
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Synthesis of the tumor associative [small alpha]-aminooxy disaccharide of the TF antigen and its conjugation to a polysaccharide immune stimulant

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1699-1702
DOI: 10.1039/C4OB00128A, CommunicationJean Paul Bourgault, Kevin R. Trabbic, Mengchao Shi, Peter R. Andreana
The [small alpha]-aminooxy derivative of the Thomsen-Friedenriech tumor-associated carbohydrate antigen has been synthesized in 11 steps. This nucleophilic sugar was then utilized in the preparation of the TF-PS A1 conjugate vaccine candidate through oxime bond formation.
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Targeting abasic site-containing DNA with annelated quinolizinium derivatives: the influence of size, shape and substituents

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1725-1734
DOI: 10.1039/C3OB42140F, PaperKatja Benner, Heiko Ihmels, Sarah Kolsch, Phil M. Pithan
A comparative analysis showed that the type and degree of annelation as well as methyl or chloro-substitution are relevant structural features that determine the interactions of quinolizinium derivatives with abasic site-containing DNA.
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Rh-catalyzed oxidative C-C bond formation and C-N bond cleavage: direct access to C2-olefinated free (NH)-indoles and pyrroles

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1703-1706
DOI: 10.1039/C3OB42605J, CommunicationSatyasheel Sharma, Sangil Han, Mirim Kim, Neeraj Kumar Mishra, Jihye Park, Youngmi Shin, Jimin Ha, Jong Hwan Kwak, Young Hoon Jung, In Su Kim
The rhodium-catalyzed oxidative C2-olefination of indoles and pyrroles containing N-arylcarboxamide directing groups with a range of alkenes and subsequent cleavage of directing groups is described.
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Copper-catalyzed decarboxylative C3-acylation of free (N-H) indoles with [small alpha]-oxocarboxylic acids

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1721-1724
DOI: 10.1039/C3OB42171F, CommunicationCuiping Wang, Shaoyan Wang, Hua Li, Jingbo Yan, Haijun Chi, Xichao Chen, Zhiqiang Zhang
A series of 3-acylindoles were synthesized by an efficient Cu-catalyzed decarboxylative C3-acylation of free (N-H) indoles with [small alpha]-oxocarboxylic acids in moderate to high yields.
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Chemical synthesis of staphyloferrin A and its application for Staphylococcus aureus detection

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1707-1710
DOI: 10.1039/C3OB41230J, CommunicationRajesh K. Pandey, Gregory G. Jarvis, Philip S. Low
The chemical synthesis of staphyloferrin A, a siderophore used by Staphylococcus bacteria for ferric iron retrieval, has been achieved with 79% yield via solid phase peptide synthesis (SPPS).
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Water promoted C-C bond cleavage: facile synthesis of 3,3-bipyrrole derivatives from dienones and tosylmethyl isocyanide (TosMIC)

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1735-1740
DOI: 10.1039/C3OB42570C, PaperRong Wang, Shun-Yi Wang, Shun-Jun Ji
Synthesis of 3,3-bipyrrole derivatives from dienones and tosylmethyl isocyanide has been reported.
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Transmembrane anion transport and cytotoxicity of synthetic tambjamine analogs

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1771-1778
DOI: 10.1039/C3OB42341G, PaperElsa Hernando, Vanessa Soto-Cerrato, Susana Cortes-Arroyo, Ricardo Perez-Tomas, Roberto Quesada
Synthetic tambjamine analogs bearing aromatic enamine moieties are highly efficient transmembrane anion carriers, triggering apoptosis in several cancer cell lines.
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Porphyrin conjugated with serum albumins and monoclonal antibodies boosts efficiency in targeted destruction of human bladder cancer cells

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1804-1811
DOI: 10.1039/C3OB42082E, PaperPatricia M. R. Pereira, Jose J. Carvalho, Sandrina Silva, Jose A. S. Cavaleiro, Rudolf J. Schneider, Rosa Fernandes, Joao P. C. Tome
The synthesis of a novel PS conjugated with bovine and human serum albumin (BSA and HSA) and a monoclonal antibody anti-CD104 is reported, as well as their biological potential against the human bladder cancer cell line UM-UC-3.
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Catalytic regioselective synthesis of pyrazole based pyrido[2,3-d]pyrimidine-diones and their biological evaluation

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1751-1758
DOI: 10.1039/C3OB42132E, PaperShailesh P. Satasia, Piyush N. Kalaria, Dipak K. Raval
Regioselective synthesis of pyrazole based pyrido[2,3-d]pyrimidine-diones using cellulose supported acidic ionic liquid (Cell-IL) as the heterogeneous catalyst.
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Unexpected regio- and chemoselectivity of cationic gold-catalyzed cycloisomerizations of propargylureas: access to tetrasubstituted 3,4-dihydropyrimidin-2(1H)-ones

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1741-1750
DOI: 10.1039/C3OB42221F, PaperOlga P. Pereshivko, Vsevolod A. Peshkov, Anatoly A. Peshkov, Jeroen Jacobs, Luc Van Meervelt, Erik V. Van der Eycken
Cationic gold-catalyzed cycloisomerizations of propargylureas for the 3,4-dihydropyrimidin-2(1H)-one core construction.
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Towards the diastereoselective synthesis of derivative of 11[prime or minute]-epi-brevipolide H

4 March, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,1793-1803
DOI: 10.1039/C3OB42367K, PaperGullapalli Kumaraswamy, Neerasa Jayaprakash, Dasa Rambabu, Aniban Ganguly, Rajkumar Banerjee
An efficient diastereoselective synthesis is accomplished employing a catalytic ATH, hydroxyl-directed cyclopropanation, catalytic epoxidation and ring closing metathesis.
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Efficient synthesis of functionalized dihydroquinolines, quinolines and dihydrobenzo[b]azepine via an iron(III) chloride-catalyzed intramolecular alkyne-carbonyl metathesis of alkyne tethered 2-amino benzaldehyde/acetophenone derivatives

2 March, 2014 - 00:17

Org. Biomol. Chem., 2014, 12,1759-1770
DOI: 10.1039/C3OB42292E, PaperSwapnadeep Jalal, Krishnendu Bera, Soumen Sarkar, Kartick Paul, Umasish Jana
Iron-catalyzed synthesis of dihydroquinolines, quinolines and dihydrobenzo[b]azepine.
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Sequential stereodivergent organocatalysis and programmed organocascades

2 March, 2014 - 00:17

Org. Biomol. Chem., 2014, 12,1681-1685
DOI: 10.1039/C3OB42310G, PerspectiveYoshihiro Sohtome, Kazuo Nagasawa
We introduce sequential dynamic asymmetric organocatalysis, focusing on diastereodivergent and enantiodivergent organocatalysis and programmed organocascades.
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Direct transformation of arylpropynes to acrylamides via a three-step tandem reaction

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1556-1560
DOI: 10.1039/C3OB42444H, CommunicationJun Qiu, Ronghua Zhang
A novel and metal-free acrylamides formation between arylpropynes and hydroxylamine hydrochloride through sp3 C-H and C-C bond cleavage has been achieved with DDQ as an oxidant.
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Towards a facile and convenient synthesis of highly functionalized indole derivatives based on multi-component reactions

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1649-1651
DOI: 10.1039/C4OB00166D, PaperConstantinos G. Neochoritis, Alexander Domling
A library of potentially bioactive compounds through the novel 1H-indole-methyl-isocyanide and MCRs has been described.
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Ketones as electrophiles in two component Baylis-Hillman reaction: a facile one-pot synthesis of substituted indolizines

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1551-1555
DOI: 10.1039/C3OB42064G, CommunicationDeevi Basavaiah, Gorre Veeraraghavaiah, Satpal Singh Badsara
2-Alkanoyl(aroyl)-pyridines were used for coupling with alkyl vinyl ketones under the influence of TMSOTf providing a facile protocol for synthesis of substituted indolizines, demonstrating the application of ketones as electrophiles in a two component Baylis-Hillman reaction.
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