Org. and Biomol. Chem.

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Performance of DFT methods and origin of stereoselectivity in bipyridine N,N[prime or minute]-dioxide catalyzed allylation and propargylation reactions

22 September, 2014 - 02:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01719F, PaperDiana Sepulveda, Tongxiang Lu, Steven E. Wheeler
It is shown that many DFT methods correctly predict the stereoselectivity of bipyridine N,N[prime or minute]-dioxide catalyzed alkylation reactions despite predicting the incorrect low-lying transition state structures. A novel explanation of the origin of stereoselectivity in these reactions is also provided.
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9-Amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts

22 September, 2014 - 02:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01648C, PaperWenwen Peng, Jingwei Wan, Bing Xie, Xuebing Ma
9-Amino-(9-deoxy)cinchona alkaloid-derived chiral phase-transfer catalysts achieved high yields (92-99%) and excellent enantioselectivities (87-96% ee) in the enantioselective [small alpha]-alkylation of glycine Schiff base.
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Synthesis of tumor-associated MUC1-glycopeptides and their multivalent presentation by functionalized gold colloids

22 September, 2014 - 02:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01339E, PaperIsabella Tavernaro, Sebastian Hartmann, Laura Sommer, Heike Hausmann, Christian Rohner, Martin Ruehl, Anja Hoffmann-Roeder, Sabine Schlecht
The authors present the synthesis of novel MUC1-glycopeptide antigens and their multivalent presentation by gold colloids. Their biological activity was tested in a dot-blot immunoassay experiment.
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Oxidative damage of aromatic dipeptides by the environmental oxidants NO2[radical dot] and O3

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01577K, PaperL. F. Gamon, J. M. White, U. Wille
Irreversible oxidative damage at both aromatic side chains and dipeptide linkage occurs in aromatic N- and C-protected dipeptides upon exposure to the environmental pollutants NO2[radical dot] and O3.
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Investigation of desilylation in the recognition mechanism to fluoride by a 1,8-naphthalimide derivative

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, Advance Article
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

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, Advance Article
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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Asymmetric total synthesis of paecilomycin E, 10[prime or minute]-epi-paecilomycin E and 6[prime or minute]-epi-cochliomycin C

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, Advance Article
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

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, Advance Article
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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The effects of CO2 pressure and pH on the Suzuki coupling of basic nitrogen containing substrates

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7598-7602
DOI: 10.1039/C4OB01630K, PaperC. Senter, A. Rumple, W. Medina-Ramos, D. Houle, Z. Cheng, C. Gelbaum, J. Fisk, B. Holden, P. Pollet, C. A. Eckert, Charles L. Liotta
The Suzuki coupling reaction of basic nitrogen containing substrates (2-bromo- and 2-chloro-4-aminopyridine, and 2-bromo and 2-chloropyridine) with phenylboronic acid using Pd(TPP)2Cl2/K3PO4 in acetonitrile-water biphasic solvent systems under a CO2 or a N2 atmosphere is discussed.
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Fast redox-triggered shuttling motions in a copper rotaxane based on a phenanthroline-terpyridine conjugate

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7572-7580
DOI: 10.1039/C4OB01206B, PaperEugenio Coronado, Pablo Gavina, Julia Ponce, Sergio Tatay
Fast shuttling motions in solution have been observed for a Cu-complexed [2] rotaxane, whose thread contains a bidentate 1,10-phenanthroline chelating unit directly connected through its 3-position to the 5-position of a tridentate 2,2[prime or minute]:6[prime or minute],2[prime or minute][prime or minute]-terpyridine.
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Enantioselective copper catalysed C-H insertion reaction of 2-sulfonyl-2-diazoacetamides to form [gamma]-lactams

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7612-7628
DOI: 10.1039/C4OB01430H, PaperLeslie Ann Clarke, Aoife Ring, Alan Ford, Abhijeet S. Sinha, Simon E. Lawrence, Anita R. Maguire
The first enantioselective copper catalysed intramolecular C-H insertion reactions of 2-sulfonyl-2-diazoacetamides is reported.
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Nitroso Diels-Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7445-7468
DOI: 10.1039/C4OB01033G, Review ArticleSerena Carosso, Marvin J. Miller
This review describes the use of nitroso Diels-Alder reactions for the functionalization of complex diene-containing natural products in order to generate libraries of compounds with potential biological activity.
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Recent developments in transition metal-catalysed spiroketalisation

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7423-7432
DOI: 10.1039/C4OB01325E, PerspectiveRachelle Quach, Daniel F. Chorley, Margaret A. Brimble
This perspective updates recent developments (since 2012) in the synthesis of spiroketals using transition metal catalysis.
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Thiomyristoyl peptides as cell-permeable Sirt6 inhibitors

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7498-7502
DOI: 10.1039/C4OB00860J, CommunicationBin He, Jing Hu, Xiaoyu Zhang, Hening Lin
Potent mechanism-based Sirt6 inhibitors.
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AcOH-mediated dichloroimination of indoles using chloramine-B: a facile access to 2,3-functionalized indolines

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7494-7497
DOI: 10.1039/C4OB01179A, CommunicationXiaozu Liu, Qinghong Hu, Zeli Yuan, Peijun Liu
A mild method for the efficient synthesis of 3,3-dichloro-2-sulfonyliminoindolines via AcOH-mediated dichloroimination of indoles using chloramine-B is described.
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Palladium-catalyzed ortho-acylation of 2-benzyl-1,2,3-triazoles with aldehydes

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7474-7477
DOI: 10.1039/C4OB01406E, CommunicationQingshan Tian, Ping He, Chunxiang Kuang
A palladium-catalyzed ortho-acylation of 2-benzyl-1,2,3-triazoles with aldehydes as an acyl source was developed. A wide variety of ketones containing 1,2,3-triazoles were obtained in good to excellent yields. This methodology provides a convenient access to the acylation of 2-substituted-1,2,3-triazoles.
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Preparation, anti-trypanosomal activity and localisation of a series of dipeptide-based vinyl sulfones

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7561-7571
DOI: 10.1039/C4OB01412J, PaperWilliam Doherty, Jinju James, Paul Evans, Laura Martin, Nikoletta Adler, Derek Nolan, Andrew Knox
An improved, Weinreb amide-based, synthesis of anti-trypanosomal lysine-containing vinyl sulfones is described incorporating, as a feature, diversity at the [varepsilon]-lysine amino group.
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Oxidative cleavage of benzylic C-N bonds under metal-free conditions

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7486-7488
DOI: 10.1039/C4OB01633E, CommunicationJin-Long Gong, Xinxin Qi, Duo Wei, Jian-Bo Feng, Xiao-Feng Wu
An interesting and practical metal-free strategy has been developed for the synthesis of aromatic aldehydes using various N,N-dimethylbenzylamines as starting materials.
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Efficient cobalt-catalyzed C-N cross-coupling reaction between benzamide and aryl iodide in water

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7478-7481
DOI: 10.1039/C4OB01483A, CommunicationBryan Yong-Hao Tan, Yong-Chua Teo
A practical and efficient strategy for the N-arylation of benzamide catalysed by a Co(C2O4)[middle dot]2H2O/dmeda system in water is reported. Under the optimized conditions, a wide variety of N-arylated products were obtained in good yields (up to 92%) using substituted aryl iodides.
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Influence of B-ring modifications on proton affinity, transmembrane anion transport and anti-cancer properties of synthetic prodigiosenes

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7515-7522
DOI: 10.1039/C4OB01399A, PaperEstelle Marchal, Soumya Rastogi, Alison Thompson, Jeffery T. Davis
We describe how modulating the pKa of a family of synthetic prodigiosenes, modified on their B-ring, can control the transmembrane transport of anions.
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