Org. and Biomol. Chem.

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Copper-catalyzed cyanation of aryl iodides with [small alpha]-cyanoacetates via C-CN bond activation

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01675D, PaperSong-Lin Zhang, Lu Huang
A mild copper-catalyzed cyanation of aryl iodides using readily available and friendly [small alpha]-cyanoacetates as the CN source is reported.
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Racemic total synthesis of dactyloidin and demethyldactyloidin through the DL-proline-catalyzed Knoevenagel condensation/[4 + 2] cycloaddition cascade

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01636C, PaperHaibo Tan, Hongxin Liu, Xinzheng Chen, Huiyu Chen, Shengxiang Qiu
An efficient approach towards the first racemic total synthesis of dactyloidin (2) and demethyldactyloidin (3) is described.
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Synthesis of trifluoromethyl [gamma]-aminophosphonates by nucleophilic aziridine ring opening

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01411E, PaperT. Cytlak, M. Saweliew, M. Kubicki, H. Koroniak
The synthesis of phosphonated derivatives of trifluoromethyl aziridines by two methods and their application in ring opening reactions have been demonstrated.
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A novel protocol for the facile construction of tetrahydroquinoline fused tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01060H, PaperManickam Bakthadoss, Varathan Vinayagam
An efficient method towards the synthesis of quinoline fused tricyclic compounds involving an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction utilizing Baylis-Hillman derivatives in good yields has been described for the first time.
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Activation of aqueous hydrogen peroxide for non-catalyzed dihydroperoxidation of ketones by azeotropic removal of water

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01503K, CommunicationK. Starkl Renar, S. Pecar, J. Iskra
Cyclic and acyclic ketones were selectively converted to gem-dihydroperoxides in 72-99% yield with 30% aq. hydrogen peroxide by azeotropic distillation of water from the reaction mixture without any catalyst.
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Synthesis of the cyanobacterial metabolite nostodione A, structural studies and potent antiparasitic activity against Toxoplasma gondii

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01506E, PaperJames McNulty, Kunal Keskar, Hilary A. Jenkins, Nick H. Werstiuk, Claudia Bordon, Robert Yolken, Lorraine Jones-Brando
A total synthesis of the cyanobacterial natural product nostodione A is reported involving a convergent, diversity-oriented route, enabling the assembly of a mini-library of structural analogues.
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Synthesis of N-dialkylphosphoryl iminosugar derivatives and their immunosuppressive activities

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01278C, CommunicationXuemei Yang, De-Cai Xiong, Chengcheng Song, Guihua Tai, Xin-Shan Ye
Twelve novel N-dialkylphosphoryliminosugar derivatives were synthesized and their immunosuppressive activities were evaluated on the proliferation of the mouse splenocytes and the secretion of IFN-[gamma] and IL-4.
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The effect of N-methylation of amino acids (Ac-X-OMe) on solubility and conformation: a DFT study

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01565K, PaperShah Md. Abdur Rauf, Per I. Arvidsson, Fernando Albericio, Thavendran Govender, Glenn E. M. Maguire, Hendrik G. Kruger, Bahareh Honarparvar
N-Methylation of amino acid derivatives (Ac-X-OMe, X = Gly, Val, Leu, Ile, Phe, Met, Cys, Ser, Asp and His) leads to an increase in aqueous solubility, lipophilicity and lowering of the cis/trans amide conformational energy barrier (EA).
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Synthesis and structure-activity relationships for cytotoxicity and apoptosis-inducing activity of (+)-halichonine B

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01488C, PaperIchiro Hayakawa, Tomomi Nakamura, Osamu Ohno, Kiyotake Suenaga, Hideo Kigoshi
(+)-Halichonine B and its analogues were synthesized, and their biological activities were evaluated. It was revealed that the secondary amino groups in the side chain portion are important for the strong cytotoxicity of halichonine B and that the N11-prenyl group is unimportant.
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Imidazoles from nitroallylic acetates and [small alpha]-bromonitroalkenes with amidines: synthesis and trypanocidal activity studies

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01444A, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.Elumalai Gopi, Tarun Kumar, Rubem F. S. Menna-Barreto, Wagner O. Valenca, Eufranio N. da Silva Junior, Irishi N. N. Namboothiri
One-pot cascade reactions of amidines with nitroallylic acetates and [small alpha]-bromonitroalkenes provide functionalized imidazoles that exhibit trypanocidal activity.
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A three-component synthesis of aryl(heteroaryl)acylamides

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01355K, PaperRafal Loska, Patrycja Bukowska
[small alpha]-Heteroarylamides of diverse structures are assembled in a three-component reaction of azole or azine N-oxides, 1,1-difluorostyrenes and amines.
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Oligonucleotides containing a ribo-configured cyclohexanyl nucleoside: probing the role of sugar conformation in base pairing selectivity

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01449B, PaperConcetta Paolella, Daniele D'Alonzo, Guy Schepers, Arthur Van Aerschot, Giovanni Di Fabio, Giovanni Palumbo, Piet Herdewijn, Annalisa Guaragna
A relationship between pairing selectivity and "sugar" conformation of six-membered nucleic acids is suggested by the study of the novel oligonucleotide system r-CNA.
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Enantioselective synthesis of monofluorinated allylic compounds: Pd-catalyzed asymmetric allylations of dimethyl 2-fluoromalonate using new N-sulfinyl-based ligands

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01434D, CommunicationNing Gao, Xiao-Ming Zhao, Cheng-Si Cai, Jue-Wang Cai
Using both new chiral S,N-ligand and dimethyl 2-fluoromalonate, Pd-catalyzed asymmetric allylic substitutions of allylic acetates with dimethyl 2-fluoromalonate were accomplished. This method produced monofluorinated allylation products in up to high yield with excellent enantioselectivity.
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One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,8993-8995
DOI: 10.1039/C5OB01462J, CommunicationVladimir A. Maslivetc, Marina Rubina, Michael Rubin
A one-pot synthesis of various GABA amides has been demostrated, employing the nucleophilic addition of primary and secondary amines across the double bond of cyclopropene-3-carboxamides, followed by ring-opening of the resulting donor-acceptor cyclopropanes and subsequent in situ reduction of enamine intermediates.
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Cu-mediated direct regioselective C-2 chlorination of indoles

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,9000-9004
DOI: 10.1039/C5OB01228G, CommunicationJing Zhao, Xiuzhi Cheng, Jun Le, Wei Yang, Fengtian Xue, Xuan Zhang, Chao Jiang
Cu-mediated C-2 chlorination of indoles was accomplished with copper(II) chloride through the use of a directing pyrimidyl protection group. A highly regioselective manner can be achieved on a range of indole substrates with excellent functional group tolerance.
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A lactate-derived chiral aldehyde for determining the enantiopurity of enantioenriched primary amines

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,9050-9054
DOI: 10.1039/C5OB01398D, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Samantha M. Gibson, Rachel M. Lanigan, Laure Benhamou, Abil E. Aliev, Tom D. Sheppard
In this paper we describe the use of a chiral aldehyde derived from lactate esters for determining the enantiopurity of primary amines, via the formation of diastereomeric imines.
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Novel insights into a major DNA oxidative lesion: its effects on Z-DNA stabilization

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,8996-8999
DOI: 10.1039/C5OB01340B, CommunicationJiaqi Wang, Shaoru Wang, Cheng Zhong, Tian Tian, Xiang Zhou
Here, we have provided novel insights into the effects of 8-oxodG substitutions on B-Z transitions of CpG dinucleotide DNAs.
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D-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,9029-9034
DOI: 10.1039/C5OB01323B, PaperA. D'Onofrio, L. Copey, L. Jean-Gerard, C. Goux-Henry, G. Pilet, B. Andrioletti, E. Framery
A novel use of D-glucosamine as chiral auxiliary for the stereoselective synthesis of phosphine oxides was developed. The three key steps of the process occurred in a stereoselective fashion.
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Triazole linker-based trivalent sialic acid inhibitors of adenovirus type 37 infection of human corneal epithelial cells

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,9194-9205
DOI: 10.1039/C5OB01025J, PaperRemi Caraballo, Michael Saleeb, Johannes Bauer, A. Manuel Liaci, Naresh Chandra, Rickard J. Storm, Lars Frangsmyr, Weixing Qian, Thilo Stehle, Niklas Arnberg, Mikael Elofsson
Adenovirus type 37 (Ad37) is one of the principal agents responsible for epidemic keratoconjunctivitis (EKC), a severe ocular infection that remains without treatment.
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Synthesis of a new class of iminosugars based on constrained azaspirocyclic scaffolds by way of catalytic C-H amination

29 August, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,9176-9180
DOI: 10.1039/C5OB01254F, CommunicationPierre-Antoine Nocquet, Raphael Hensienne, Joanna Wencel-Delord, Eric Wimmer, Damien Hazelard, Philippe Compain
High level of regiocontrol has been achieved in the C-H amination of substrates with a high density of reactive C-H bonds, allowing the access to a new class of conformationally constrained iminosugars.
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