Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Total synthesis of a thromboxane receptor antagonist, terutroban

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02302A, PaperWasim Ahmed, Prathama S. Mainkar, Srihari Pabbaraja, Srivari Chandrasekhar
Synthesis of terutroban (2) is achieved following a non-Diels-Alder approach using cost-effective chemicals.
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Synthesis of 7-alkylidene-7,12-dihydroindolo[3,2-d]benzazepine-6-(5H)-ones (7-alkylidene-paullones) by N-cyclization-oxidative Heck cascade and characterization as sirtuin modulators

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02493A, PaperJ. G. Denis, G. Franci, L. Altucci, J. M. Aurrecoechea, A. R. de Lera, R. Alvarez
A palladium-induced cascade of N-cyclization and oxidative Heck reaction of o-alkynylanilines produced 7-alkylidene-indolobenzazepinones (paullones) that have sirtuin modulation activities.
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Highly regio- and diastereo-selective synthesis of novel tri- and tetra-cyclic perhydroquinoline architectures via an intramolecular [3 + 2] cycloaddition reaction

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02203C, CommunicationM. Bakthadoss, D. Kannan, J. Srinivasan, V. Vinayagam
A facile and efficient synthetic protocol was established for the construction of novel tri- and tetra-cyclic pyrrolo/pyrrolizinoquinoline architectures via an intramolecular [3 + 2] cycloaddition reaction strategy.
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Conformational properties of 1,4- and 1,5-substituted 1,2,3-triazole amino acids - building units for peptidic foldamers

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02359E, PaperNina Kann, Johan R. Johansson, Tamas Beke-Somfai
Conformational diversity of 1,4- and 1,5-substituted 1,2,3-triazole amino acids makes them promising building units for novel peptidic foldamers.
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Asymmetric metal free [small beta]-boration of [small alpha],[small beta]-unsaturated imines assisted by (S)-MeBoPhoz

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1328-1332
DOI: 10.1039/C4OB02478H, CommunicationEnrico La Cascia, Xavier Sanz, Carles Bo, Andrew Whiting, Elena Fernandez
The adduct [MeO [rightward arrow] Bpin-Bpin]- efficiently mediates the [small beta]-boration of [small alpha],[small beta]-unsaturated imines formed in situ.
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Acid-promoted transformations of 1-(diphenylphosphoryl)allenes: synthesis of novel 1,4-dihydrophosphinoline 1-oxides

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1333-1338
DOI: 10.1039/C4OB02269F, CommunicationAlexander S. Bogachenkov, Albina V. Dogadina, Vadim P. Boyarskiy, Aleksander V. Vasilyev
1-(Diphenylphosphoryl)alka-1,2-dienes in acids (TfOH, FSO3H, H2SO4) give (3-hydroxyalk-1-en-1-yl)diphenylphosphine oxides, that are further converted into 1-phenyl-1,4-dihydrophosphinoline 1-oxides. The latter compounds are directly formed from these 1,2-dienes under the action of AlCl3.
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Copper-catalyzed O-arylation of N-protected 1,2-aminoalcohols using functionalized trivalent organobismuth reagents

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1322-1327
DOI: 10.1039/C4OB02497D, CommunicationPauline Petiot, Julien Dansereau, Martin Hebert, Imene Khene, Tabinda Ahmad, Samira Samaali, Maxime Leroy, Francis Pinsonneault, Claude Y. Legault, Alexandre Gagnon
The O-arylation of 1,2-aminoalcohols using functionalized triarylbismuth reagents is reported.
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"AND" luminescent "reactive" molecular logic gates: a gateway to multi-analyte bioimaging and biosensing

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1294-1306
DOI: 10.1039/C4OB02076F, Review ArticleAnthony Romieu
This feature article focuses on the recent development of "AND" luminescent molecular logic gates, in which the optical output is produced in response to multiple (bio)chemical inputs and through cascades of covalent bond-modifying reactions triggered by target (bio)analytes, for biosensing and bioimaging applications in complex media.
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Consecutive three-component synthesis of (hetero)arylated propargyl amides by chemoenzymatic aminolysis-Sonogashira coupling sequence

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1571-1576
DOI: 10.1039/C4OB02386B, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.Sidra Hassan, Anja Ullrich, Thomas J. J. Muller
(Hetero)arylated propargyl amides are efficiently prepared by consecutive chemoenzymatic three-component synthesis based upon lipase catalyzed aminolysis followed by Sonogashira coupling.
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E- or Z-Selective synthesis of 4-fluorovinyl-1,2,3-triazoles with fluorinated second-generation Julia-Kocienski reagents

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1536-1549
DOI: 10.1039/C4OB02179G, PaperRakesh Kumar, Govindra Singh, Louis J. Todaro, Lijia Yang, Barbara Zajc
Second-generation Julia-Kocienski reagents from CuAAC reactions of [small alpha]-fluoropropargyl benzothiazole sulfone with azides, react with aldehydes and ketones to give N-substituted 4-(1-fluorovinyl)triazoles. Reactions of aldehydes can be tuned towards E or Z-alkenes selectively.
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Stereoselective synthesis of fluorinated aminoglycosyl phosphonates

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1317-1321
DOI: 10.1039/C4OB02317J, CommunicationSanne Bouwman, Romano V. A. Orru, Eelco Ruijter
We report the highly stereoselective addition of lithiated difluorophosphonates to nitroglycals, providing synthetic access to biologically relevant fluorinated aminoglycosyl phosphonates.
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Synthesis and antimalarial evaluation of amide and urea derivatives based on the thiaplakortone A natural product scaffold

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1558-1570
DOI: 10.1039/C4OB01849D, PaperBrett D. Schwartz, Tina S. Skinner-Adams, Katherine T. Andrews, Mark J. Coster, Michael D. Edstein, Donna MacKenzie, Susan A. Charman, Maria Koltun, Scott Blundell, Anna Campbell, Rebecca H. Pouwer, Ronald J. Quinn, Karren D. Beattie, Peter C. Healy, Rohan A. Davis
A series of amide and urea analogues based on the thiaplakortone A natural product scaffold were synthesised and screened for in vitro antimalarial activity.
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Linear dialdehydes as promising substrates for aminocatalyzed transformations

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1280-1293
DOI: 10.1039/C4OB01805B, Review ArticleIndresh Kumar, Panduga Ramaraju, Nisar A. Mir, Anoop Singh
Linear dialdehydes: This article summarizes the recent utilization of linear dialdehydes as appropriate substrates for amine catalyzed cascade/domino transformations.
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Synthesis and antitumor activity of novel 2-substituted indoline imidazolium salt derivatives

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1550-1557
DOI: 10.1039/C4OB02385D, PaperXiao-Liang Xu, Chun-Lei Yu, Wen Chen, Ying-Chao Li, Li-Juan Yang, Yan Li, Hong-Bin Zhang, Xiao-Dong Yang
A series of novel 2-substituted indoline imidazolium salt derivatives were synthesized and their antitumor structure-activity relationship studies were reported.
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N-heterocyclic carbene-catalyzed cyclocondensation of 2-aryl carboxylic acids and enones: highly enantioselective synthesis of [small delta]-lactones

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1313-1316
DOI: 10.1039/C4OB02330G, CommunicationJin-Tang Cheng, Xiang-Yu Chen, Song Ye
The NHC-catalyzed [4 + 2] cyclocondensation of 2-aryl carboxylic acids with enones was developed, giving [small delta]-lactones in good yields with high enantioselectivities.
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Pd-catalyzed Heck-conjoined amidation and concomitant chemoselective Michael-addition: an efficient tandem approach to highly functionalized tetrahydroquinazolines from o-haloanilines

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1521-1530
DOI: 10.1039/C4OB02286F, PaperRakesh K. Saunthwal, Monika Patel, Abhinandan K. Danodia, Akhilesh K. Verma
Efficient palladium-catalyzed tandem approach for the synthesis of highly functionalized tetrahydroquinazolines from o-haloanilines with acrylates and isothiocyanates/isocyanates via Heck-conjoined amidation/thioamidation and concomitant chemoselective Michael-addition is described.
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A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1515-1520
DOI: 10.1039/C4OB02147A, PaperShuo Xing, James L. Gleason
Glycal etherification followed by azidonitration/reduction solves a difficult SN2 step in the synthesis of N-glycolyl muramyl dipeptide.
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Domino reaction involving the Bestmann-Ohira reagent and [small alpha],[small beta]-unsaturated aldehydes: efficient synthesis of functionalized pyrazoles

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1492-1499
DOI: 10.1039/C4OB02365J, PaperShakir Ahamad, Ashis Kumar Gupta, Ruchir Kant, Kishor Mohanan
A mild, efficient and rapid domino reaction involving the Bestmann-Ohira reagent (BOR) and [small alpha],[small beta]-unsaturated aldehydes has been developed for the synthesis of densely functionalized vinylpyrazoles.
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A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: design, synthesis, and biological evaluation

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1507-1514
DOI: 10.1039/C4OB01605J, PaperGaofei Wei, Weijing Luan, Shuai Wang, Shanshan Cui, Fengran Li, Yongxiang Liu, Yang Liu, Maosheng Cheng
A series of novel oleanolic acid coupled 1,2,3-triazole derivatives have been designed and synthesized by employing a Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition reaction.
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Accelerated Fmoc solid-phase synthesis of peptides with aggregation-disrupting backbones

27 January, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,1500-1506
DOI: 10.1039/C4OB02260B, PaperYi-Chao Huang, Chao-Jian Guan, Xiang-Long Tan, Chen-Chen Chen, Qing-Xiang Guo, Yi-Ming Li
In this work, we describe an accelerated solid-phase synthetic protocol for ordinary or difficult peptides involving air-bath heating and amide protection.
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