Org. and Biomol. Chem.

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Lipase-catalyzed asymmetric synthesis of oxathiazinanones through dynamic covalent kinetic resolution

19 May, 2014 - 19:17

Org. Biomol. Chem., 2014, 12,3572-3575
DOI: 10.1039/C4OB00365A, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.Lei Hu, Yan Zhang, Olof Ramstrom
A domino addition-lactonization pathway has been applied to a dynamic covalent resolution protocol, leading to efficient asymmetric synthesis of oxathiazinanones.
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Silyl alkynylphosphine-boranes: key precursors of triazolylphosphines via tandem desilylation-Click chemistry

19 May, 2014 - 19:17

Org. Biomol. Chem., 2014, 12,3635-3640
DOI: 10.1039/C4OB00397G, PaperRomain Veillard, Elise Bernoud, Ibrahim Abdellah, Jean-Francois Lohier, Carole Alayrac, Annie-Claude Gaumont
A versatile synthesis of P-stereogenic 1,2,3-triazolyl-4-phosphines from the borane complexes of phosphino-alkynes has been developed.
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An enantioselective strategy for the total synthesis of (S)-tylophorine via catalytic asymmetric allylation and a one-pot DMAP-promoted isocyanate formation/Lewis acid catalyzed cyclization sequence

19 May, 2014 - 19:17

Org. Biomol. Chem., 2014, 12,3616-3621
DOI: 10.1039/C4OB00200H, PaperBo Su, Hui Zhang, Meng Deng, Qingmin Wang
A novel total synthesis of (S)-tylophorine is reported, featuring asymmetric allylation and cascade isocyanate formation and cyclization.
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A porphyrin/[small beta]-cyclodextrin conjugated nano-system having a pan-lid molecular structure for smart drug carrier applications

19 May, 2014 - 19:17

Org. Biomol. Chem., 2014, 12,3663-3670
DOI: 10.1039/C4OB00393D, PaperPlacido Mineo
In this study, 5,10,15-tri[p(9-methoxy-triethyleneoxy)phenyl]-20-[p-phenylisophthalate-[small beta]-cyclodextrin]porphyrin, a compound containing a porphyrin and a [small beta]-cyclodextrin unit covalently linked by means of an isophthalic bridge, was synthesized and characterized by NMR, MALDI-TOF, UV-vis and CD techniques.
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Catalytic, enantioselective vinylogous Michael reactions

19 May, 2014 - 19:17

Org. Biomol. Chem., 2014, 12,3531-3543
DOI: 10.1039/C4OB00332B, Review ArticleChristoph Schneider, Falko Abels
Recent progress towards catalytic, enantioselective vinylogous Michael reactions is presented which deliver optically highly enriched 1,7-dioxo compounds of great utility in organic synthesis.
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Gorlos-Phos for palladium-catalyzed borylation of aryl chlorides

19 May, 2014 - 19:17

Org. Biomol. Chem., 2014, 12,3604-3610
DOI: 10.1039/C4OB00293H, PaperPengbin Li, Chunling Fu, Shengming Ma
Using a readily available form of the mono-phosphine ligand, Gorlos-Phos[middle dot]HBF4, Pd-catalyzed borylation of aryl chlorides afforded aryl boronates in high yields.
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Self-assembly of peptides to nanostructures

19 May, 2014 - 19:17

Org. Biomol. Chem., 2014, 12,3544-3561
DOI: 10.1039/C4OB00447G, Review ArticleDindyal Mandal, Amir Nasrolahi Shirazi, Keykavous Parang
The formation of well-ordered nanostructures through self-assembly of diverse organic and inorganic building blocks has drawn much attention owing to their potential applications in biology and chemistry.
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Microwave-assisted one-pot synthesis and anti-biofilm activity of 2-amino-1H-imidazole/triazole conjugates

19 May, 2014 - 19:17

Org. Biomol. Chem., 2014, 12,3671-3678
DOI: 10.1039/C3OB42282H, PaperHans Steenackers, Denis Ermolat'ev, Tran Thi Thu Trang, Bharat Savalia, Upendra K. Sharma, Ami De Weerdt, Anamik Shah, Jozef Vanderleyden, Erik V. Van der Eycken
A microwave-assisted protocol was developed for the construction of 2-amino-1H-imidazole/triazole conjugates with anti-biofilm activity.
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A novel synthetic approach to the bicyclo[5.3.1]undecan-11-one framework of vinigrol

19 May, 2014 - 19:17

Org. Biomol. Chem., 2014, 12,3562-3566
DOI: 10.1039/C4OB00046C, CommunicationXian-Lei Wang, Yun-Yu Lu, Jie Wang, Xuan Wang, He-Quan Yao, Guo-Qiang Lin, Bing-Feng Sun
A unique approach to the [5.3.1] bicyclic core of vinigrol is described featuring highly stereoselective C-C bond forming reactions through exploring the inherent conformational bias of the cyclooctane-ring system.
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Characterisation of radicals formed by the triazine 1,4-dioxide hypoxia-activated prodrug, SN30000

17 May, 2014 - 18:54

Org. Biomol. Chem., 2014, 12,3386-3392
DOI: 10.1039/C4OB00236A, PaperRobert F. Anderson, Pooja Yadav, Deepa Patel, Johannes Reynisson, Smitha R. Tipparaju, Christopher P. Guise, Adam V. Patterson, William A. Denny, Andrej Maroz, Sujata S. Shinde, Michael P. Hay
One-electron bioreduction of SN30000, a triazine 1,4-dioxide anticancer drug, forms reactive aryl and carbon-centred radicals.
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Strategies for the construction of tetrahydropyran rings in the synthesis of natural products

17 May, 2014 - 18:54

Org. Biomol. Chem., 2014, 12,3323-3335
DOI: 10.1039/C4OB00423J, Review ArticleNadiah Mad Nasir, Kristaps Ermanis, Paul A. Clarke
This review focuses on the methodology used for the construction of tetrahydropyran (THP) rings in the synthesis of natural products over the last seven years.
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Direct olefination of benzaldehydes into 1,3-diarylpropenes via a copper-catalyzed heterodomino Knoevenagel-decarboxylation-Csp3-H activation sequence

17 May, 2014 - 18:54

Org. Biomol. Chem., 2014, 12,3493-3498
DOI: 10.1039/C4OB00155A, PaperYaping Zhao, Lu Sun, Tieqiang Zeng, Jiayi Wang, Yanqing Peng, Gonghua Song
Copper-catalyzed direct olefination of benzaldehydes into unsymmetrical 1,3-diarylpropenes by a novel domino Knoevenagel-decarboxylation-Csp3-H activation sequence using simpler substrates like benzaldehydes.
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Diastereoselective formation of aziridines from diazocarbonyl compounds and N-(O-pivaloylated D-galactosyl)benzylideneamines and ring-opening reactions with p-toluenethiol

17 May, 2014 - 18:54

Org. Biomol. Chem., 2014, 12,3362-3365
DOI: 10.1039/C4OB00443D, CommunicationYizhou Zhao, Gang Wang, Shanshan Zhou, Zhongjun Li, Xiangbao Meng
N-Galactosyl aziridines were synthesized, and the ring-opening reactions provided enantiometrically pure [small beta]-S-substituted phenylalanine derivatives with high regioselectivity.
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Synthesis and gene transfection activity of cyclen-based cationic lipids with asymmetric acyl-cholesteryl hydrophobic tails

17 May, 2014 - 18:54

Org. Biomol. Chem., 2014, 12,3484-3492
DOI: 10.1039/C4OB00384E, PaperBao-Quan Liu, Wen-Jing Yi, Ji Zhang, Qiang Liu, Yan-Hong Liu, Sheng-Di Fan, Xiao-Qi Yu
Novel cyclen-based cationic lipids with asymmetric acyl-cholesteryl hydrophobic tails were synthesized and applied as non-viral gene vectors.
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Synthesis of N-alkyl isatins via oxidative cyclization of N-alkyl 2-bromo(chloro)acetanilides

17 May, 2014 - 18:54

Org. Biomol. Chem., 2014, 12,3349-3353
DOI: 10.1039/C4OB00118D, CommunicationQingwen Gui, Fenglin Dai, Jidan Liu, Peixing Chen, Zhiyong Yang, Xiang Chen, Ze Tan
N-Alkyl isatins were synthesized via oxidative cyclization of N-alkyl 2-bromo or 2-chloro acetanilides in DMSO.
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Carbohydrate-based first stereoselective total synthesis of bioactive cytospolide P

17 May, 2014 - 18:54

Org. Biomol. Chem., 2014, 12,3358-3361
DOI: 10.1039/C4OB00323C, CommunicationPathi Suman, Bhimapaka China Raju
A facile stereoselective approach has been developed for the total synthesis of cytospolide P via Yamaguchi macrolactonization.
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A simple structural hydrazide-based gelator as a fluoride ion colorimetric sensor

17 May, 2014 - 18:54

Org. Biomol. Chem., 2014, 12,3478-3483
DOI: 10.1039/C4OB00056K, PaperBinglian Bai, Jie Ma, Jue Wei, Jianxi Song, Haitao Wang, Min Li
The C8 organogel could show reversible gel-sol transition and color changes by the use of F- stimuli and proton control.
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Design, synthesis and evaluation of seleno-dihydropyrimidinones as potential multi-targeted therapeutics for Alzheimer's disease

17 May, 2014 - 18:54

Org. Biomol. Chem., 2014, 12,3470-3477
DOI: 10.1039/C4OB00598H, PaperRomulo F. S. Canto, Flavio A. R. Barbosa, Vanessa Nascimento, Aldo S. de Oliveira, Ines M. C. Brighente, Antonio Luiz Braga
We report the design, synthesis and evaluation of a series of seleno-dihydropyrimidinones as potential multi-targeted therapeutics for Alzheimer's disease.
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Benzo[a]acridinylmethyl esters as pH sensitive fluorescent photoactive precursors: synthesis, photophysical, photochemical and biological applications

15 May, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,3459-3469
DOI: 10.1039/C3OB42600A, PaperMohammed Ikbal, Biswajit Saha, Shrabani Barman, Sanghamitra Atta, Deb Ranjan Banerjee, Sudip Kumar Ghosh, N. D. Pradeep Singh
(Benzo[a]acridin-12-yl)methyl (BAM) chromophore has been shown to perform dual functions as a "pH sensitive fluorescent probe" and a "phototrigger" for acids.
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A multicomponent approach to the synthesis of N-sulfonyl [small beta]2,3-amino esters

15 May, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,3423-3426
DOI: 10.1039/C3OB42353K, PaperErwan Le Gall, Stephane Sengmany, Issa Samb, Sabrina Benakrour, Christopher Colin, Antoine Pignon, Eric Leonel
The multicomponent synthesis of [small alpha],[small beta]-disubstituted N-sulfonyl [small beta]-amino esters is described.
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