Org. and Biomol. Chem.

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Enantioselective total syntheses of the proposed structures of prevezol B and evaluation of anti-cancer activity

10 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8239-8246
DOI: 10.1039/C4OB01662A, PaperAnna E. Leung, Riccardo Rubbiani, Gilles Gasser, Kellie L. Tuck
The first enantioselective total syntheses of the proposed structures of the natural product prevezol B are reported. This work has shown that the proposed structures of prevezol B are incorrect.
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Investigation of desilylation in the recognition mechanism to fluoride by a 1,8-naphthalimide derivative

10 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8275-8279
DOI: 10.1039/C4OB01500B, PaperJeeun Woo, Gunwoo Kim, Kevanie Quintero, Michael P. Hanrahan, Hector Palencia, Haishi Cao
Desilylation based fluorescence sensor (AF-1) gives a dual signal for quantitative detection of F- in MeCN.
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Annulated and bridged tetrahydrofurans from alkenoxyl radical cyclization

10 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8288-8307
DOI: 10.1039/C4OB01266F, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Christine Schur, Harald Kelm, Thomas Gottwald, Arne Ludwig, Rainer Kneuer, Jens Hartung
4-Pentenoxyl radicals sharing two or more carbon atoms with a cycloalkane cyclize in a predictable manner stereoselectively and regioselectively to afford in solutions of bromotrichloromethane cycloalkyl-fused or -bridged 2-bromomethyltetrahydrofurans in up to 95% yield.
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Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles

10 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8204-8211
DOI: 10.1039/C4OB00978A, PaperJiuxi Chen, Leping Ye, Weike Su
Synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines and 7-benzoylindoles.
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Pd-Catalyzed Oxidative C-H Alkenylation for Synthesizing Arylvinyltriazole Nucleosides

8 October, 2014 - 06:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01836B, PaperJingjie Tang, Mei Cong, Yi Xia, Gilles Quelever, Yuting Fan, Fanqi Qu, Ling Peng
Various arylvinyltriazole nucleoside analogues were synthesized using Pd-catalyzed oxidative Heck reaction. This method affords the corresponding and otherwise difficult to achieve arylvinyltriazole nucleosides with good yields and large functional group...
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Addition of Optically Pure H-Phosphinate to Ketones: the Selectivity, Stereochemistry and Mechanism

8 October, 2014 - 06:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01574F, PaperChang-Qiu Zhao, Yong-Ming Sun, Nana Xin, Zhong-Yuan Xu, Li-Juan Liu, Fan-Jie Meng, He Zhang, Bao-Ci Fu, Qiu-Ju Liang, Hong-Xing Zheng, Li-Jun Sun, Li-Biao Han
Aromatic methyl ketones and cyclic asymmetric ketones underwent hydrophosphorylation with P-stereogenic H-P species in the presence of potassium carbonate to produce P,C-stereogenic tertiary [small alpha]-hydroxyl phosphinates in excellent yields and up...
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Catalytic Asymmetric Desymmetrization Approach to Enantioenriched Cyclopentanes

8 October, 2014 - 06:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01649A, PerspectiveMadhu Sudan Manna, Santanu Mukherjee
Catalytic asymmetric desymmetrization represents an excellent strategy for accessing highly functionalized chiral building blocks. However, the application of desymmetrization for the synthesis of enantioenriched cyclopentane derivatives remained limited, when compared...
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Phosphonated Chelates for Nuclear Imaging

8 October, 2014 - 06:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01514B, PaperCaline Christine, Laurence Sabatier, Sabah Abada, Alexandre Lecointre, Gertraud Orend, Patrice Laquerriere, David Brasse, Mourad Elhabiri, Ali Ouadi, Thomas Hussenet, Falk Saupe, L. J. Charbonniere
A series of bis-, tris- and tetra-phosphonated pyridine ligands is presented. In view of their potential as chelates for radiopharmaceutical applications, the physico-chemical properties of the ligands and of their...
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Glucuronidation of Bile Acids under Flow Conditions: Design of Experiments and Koenigs-Knorr Reaction Optimization

8 October, 2014 - 06:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01911C, PaperSerena Mostarda, Paolo Filipponi, Roccaldo Sardella, Francesco Venturoni, Benedetto Natalini, Roberto Pellicciari, Antimo Gioiello
An efficient method for the C3-glucuronidation of bile acids has been developed under flow conditions. A modular mesoreactor assisted flow set-up was combined with statistical design of experiments to speed...
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The design, synthesis and biological evaluation of novel thiamin diphosphate analog inhibitors against the pyruvate dehydrogenase multienzyme complex E1 from Escherichia coli

8 October, 2014 - 06:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01347F, PaperLingling Feng, Junbo He, Haifeng He, Lulu Zhao, Lingfu Deng, Li Zhang, Lin Zhang, Yanliang Ren, Jian Wan, Hongwu He
Optimal binding mode for the novel potent inhibitor 4j against PDHc-E1 from E. coli.
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Solvent switchable cycloaddition: a (one-pot) metal-free approach towards N-substituted benzo[e]- or [f]isoindolones via Csp2-H functionalization

8 October, 2014 - 06:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01644K, PaperPratik A. Ambasana, Dipak D. Vachhani, Marzia Galli, Jeroen Jacobs, Luc Van Meervelt, Anamik K. Shah, Erik V. Van der Eycken
Solvent steers the selectivity: Green and practical Csp2-H functionalization towards N-substituted benzo[e]- or [f]isoindolones.
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The impact of LR-HSQMBC very long-range heteronuclear correlation data on computer-assisted structure elucidation

8 October, 2014 - 06:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01418A, CommunicationK. A. Blinov, A. V. Buevich, R. T. Williamson, G. E. Martin
The impact of LR-HSQMBC very long-range nJCH heteronuclear shift correlation data as a supplement to HMBC data as input for the computer-assisted structure elucidation program, Structure Elucidator[registered sign], is assessed for the first time.
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Highly diastereoselective 1,3-dipolar cycloadditions of chiral non-racemic nitrones to 1,2-diaza-1,3-dienes: an experimental and computational investigation

8 October, 2014 - 06:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01371A, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Roberta Majer, Olga Konechnaya, Ignacio Delso, Tomas Tejero, Orazio A. Attanasi, Stefania Santeusanio, Pedro Merino
Asymmetric 1,3-dipolar cycloadditions between 1,2-diaza-1,3-dienes and chiral non-racemic nitrones to give 3-substituted-5-diazenyl isoxazolidines were studied.
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Clicked bis-PEG-peptide conjugates for studying calmodulin-Kv7.2 channel binding

8 October, 2014 - 06:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01338G, PaperM. Angeles Bonache, Alessandro Alaimo, Covadonga Malo, Oscar Millet, Alvaro Villarroel, Rosario Gonzalez-Muniz
Small bis-conjugates helix A329-350-PEG-triazole-PEG-helix B508-526 (41 residues), prepared through click chemistry of PEGylated peptide derivatives, bind to CaM with nanomolar affinity, behaving as mimics of the Kv7.2 native fragment (239 residues).
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Stability and bioactivity of thrombin binding aptamers modified with D-/L-isothymidine in the loop regions

8 October, 2014 - 06:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01525H, PaperBaobin Cai, Xiantao Yang, Lidan Sun, Xinmeng Fan, Liyu Li, Hongwei Jin, Yun Wu, Zhu Guan, Liangren Zhang, Lihe Zhang, Zhenjun Yang
D-/L-IsoT were used to modify the loop regions of TBA and greatly improved its bioactivity as well as stability.
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Imides modified benzopicenes: synthesis, solid structure and optoelectronic properties

8 October, 2014 - 06:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01486C, PaperDi Wu, Haojie Ge, Zhao Chen, Jinhua Liang, Jie Huang, Yufeng Zhang, Xiaoqiang Chen, Xianggao Meng, Sheng Hua Liu, Jun Yin
Imide-modified polycyclic aromatic hydrocarbons can be widely applied in the field of optoelectronic materials.
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Asymmetric total synthesis of paecilomycin E, 10[prime or minute]-epi-paecilomycin E and 6[prime or minute]-epi-cochliomycin C

8 October, 2014 - 06:17

Org. Biomol. Chem., 2014, 12,8257-8274
DOI: 10.1039/C4OB01400F, PaperPratik Pal, Nandan Jana, Samik Nanda
The asymmetric total syntheses of paecilomycin E and its stereoisomers have been disclosed by employing the late stage Mitsunobu macrolactonization reaction.
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Synthesis and SARs of indole-based [small alpha]-amino acids as potent HIV-1 non-nucleoside reverse transcriptase inhibitors

8 October, 2014 - 06:17

Org. Biomol. Chem., 2014, 12,8308-8317
DOI: 10.1039/C4OB01333F, PaperXin Han, Haoming Wu, Wei Wang, Chune Dong, Po Tien, Shuwen Wu, Hai-Bing Zhou
Indole-based [small alpha]-amino acids as potent non-nucleoside reverse transcriptase inhibitors (NNRTIs) of HIV-1 have been developed using a TZM-bl cell assay on HIV virus type HIV-1IIIB. A comprehensive SAR study of these indole [small alpha]-amino acids was also presented.
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Subtle Mitsunobu couplings under super-heating: the role of high-throughput continuous flow and microwave strategies

8 October, 2014 - 06:17

Org. Biomol. Chem., 2014, 12,8112-8124
DOI: 10.1039/C4OB01432D, Review ArticleAtul Manvar, Anamik Shah
Fragile Mitsunobu reaction can efficiently be performed under super-heating.
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Regiodivergent and short total synthesis of calothrixins

8 October, 2014 - 06:17

Org. Biomol. Chem., 2014, 12,8196-8203
DOI: 10.1039/C4OB01309C, PaperDipakranjan Mal, Joyeeta Roy, Kumar Biradha
The anionic annulation of MOM-protected furoindolone with 4-bromoquinoline followed by deprotection of the N-MOM group provides calothrixin B, whereas that with 3-bromoquinoline yields isocalothrixin B. The outcomes are explained by the divergence of the reaction mechanism from the commonly perceived 3,4-didehydroquinoline. A sequence of addition-cyclization-elimination is proposed to account for the formation of calothrixin from 4-bromoquinoline.
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