Royal Society of Chemistry

Synthesis of novel symmetrical 2-oxo-spiro[indole-3,4[prime or minute]-pyridines] by a reaction of oxindoles with 1,2-diaza-1,3-dienes

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01959H, PaperOrazio A. Attanasi, Linda A. Campisi, Lucia De Crescentini, Gianfranco Favi, Fabio Mantellini
Synthesis of symmetrical 2-oxo-spiro[indole-3,4[prime or minute]-pyridines]: a novel example of spirocyclic oxindoles bearing a quaternary centre at the 3-position.
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Copper-catalysed [small alpha]-selective allylic alkylation of heteroaryllithium reagents

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9321-9323
DOI: 10.1039/C4OB01896F, CommunicationCarlos Vila, Valentin Hornillos, Martin Fananas-Mastral, Ben L. Feringa
2-Allyl-substituted thiophenes and furans are synthesised efficiently in a direct procedure using 2-heteroaryllithium reagents and allyl bromides and chlorides catalysed by ligand-free copper(I). The reactions take place under mild conditions, with excellent [small alpha]-selectivity, high functional group tolerance and good yields for the SN2 products.
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First total synthesis of ganglioside DSG-A possessing neuritogenic activity

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9345-9349
DOI: 10.1039/C4OB01882F, CommunicationYu-Fa Wu, Yow-Fu Tsai, Jhe-Ruei Guo, Cheng-Ping Yu, Hui-Ming Yu, Chun-Chen Liao
The first total synthesis of ganglioside DSG-A (1) is achieved via chemoselective glycosylation and a [1 + 1 + 2] synthetic strategy.
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Remote conformational control of a molecular switch via methylation and deprotonation

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9384-9388
DOI: 10.1039/C4OB01991A, PaperPeter C. Knipe, Ian M. Jones, Sam Thompson, Andrew D. Hamilton
Methylation and deprotonation at remote sites of a diphenylacetylene-based molecular switch exert global conformational changes through subtle tuning of a hydrogen-bonding network.
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Magnetic resonance and optical imaging probes for NMDA receptors on the cell surface of neurons: synthesis and evaluation in cellulo

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9389-9404
DOI: 10.1039/C4OB01848F, PaperNeil Sim, Robert Pal, David Parker, Joern Engelmann, Anurag Mishra, Sven Gottschalk
A second generation of N-methyl-D-aspartate (NMDA) receptor-targeted MRI contrast agents has been synthesised, based on bicyclic NMDA receptor antagonists and show selective and reversible cell-surface binding.
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Total syntheses of cis-cyclopropane fatty acids: dihydromalvalic acid, dihydrosterculic acid, lactobacillic acid, and 9,10-methylenehexadecanoic acid

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9427-9438
DOI: 10.1039/C4OB01863J, PaperSayali Shah, Jonathan M. White, Spencer J. Williams
A systematic approach to the synthesis of enantiomeric pairs of the four title cis-cyclopropane fatty acids is reported.
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Highly regioselective synthesis of 3-alkenyl-oxindole ring-fused 3,3[prime or minute]-disubstituted oxindoles via direct gamma-substitution of Morita-Baylis-Hillman carbonates of isatins with 3-substituted oxindoles

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9366-9374
DOI: 10.1039/C4OB01523A, PaperTing-Ting Feng, Xuan Huang, Xiong-Li Liu, De-Hong Jing, Xiong-Wei Liu, Feng-Ming Guo, Ying Zhou, Wei-Cheng Yuan
The synthesis and antitumor activity evaluation of 3-alkenyl-oxindole ring-fused 3,3[prime or minute]-disubstituted oxindoles.
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One pot synthesis of pyrrolo[3,4-c]quinolinone/pyrrolo[3,4-c]quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC)

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9471-9477
DOI: 10.1039/C4OB01580K, PaperXin-Mou Lu, Jian Li, Zhong-Jian Cai, Rong Wang, Shun-Yi Wang, Shun-Jun Ji
An efficient and practical synthetic approach giving access to 2H-pyrrolo[3,4-c]quinolin-4(5H)-one/2H-pyrrolo[3,4-c]quinoline derivatives via a one pot van Leusen reaction and cyclization under basic conditions.
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Palladium-catalyzed coupling of N-tosylhydrazones and [small beta]-bromostyrene derivatives: new approach to 2H-chromenes

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9333-9336
DOI: 10.1039/C4OB01979B, CommunicationYamu Xia, Ying Xia, Yan Zhang, Jianbo Wang
A palladium-catalyzed cascade reaction that involves [small pi]-allylic palladium species generated from carbene migratory insertion leads to the formation of 2H-chromenes.
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Thiol-assisted one-pot synthesis of peptide/protein C-terminal thioacids from peptide/protein hydrazides at neutral conditions

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9413-9418
DOI: 10.1039/C4OB01885K, PaperChenchen Chen, Yichao Huang, Ling Xu, Yong Zheng, Huajian Xu, Qingxiang Guo, Changlin Tian, Yiming Li, Jing Shi
An efficient thiol-assisted one-pot synthesis of peptide/protein C-terminal thioacids was achieved by using peptide/protein hydrazides precursors at neutral pH and room temperature (about 20 [degree]C).
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A review of methods to synthesise 4[prime or minute]-substituted nucleosides

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9291-9306
DOI: 10.1039/C4OB01449A, Review ArticleMark Betson, Nigel Allanson, Philip Wainwright
Modified nucleosides have received a great deal of attention from the scientific community, either for use as therapeutic agents, diagnostic tools, or as molecular probes.
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Rhodium(III)-catalyzed C-H alkynylation of azomethine ylides under mild conditions

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9329-9332
DOI: 10.1039/C4OB01596G, CommunicationXueyun Zhang, Zisong Qi, Jian Gao, Xingwei Li
Rh(III) complexes catalyzed the ortho C-H alkynylation of azomethine imine, which acts as a masked aldehyde group.
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Addition of optically pure H-phosphinate to ketones: selectivity, stereochemistry and mechanism

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9457-9465
DOI: 10.1039/C4OB01574F, PaperYong-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, Chang-Qiu Zhao, Li-Biao Han
A stability-controlled diastereoselective addition of a chiral P-H species to ketones afforded P,C-stereogenic [small alpha]-hydroxyphosphinates in excellent yields and dr.
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Asymmetric organocatalytic SOMO reactions of enol silanes and silyl ketene (thio)acetals

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9446-9452
DOI: 10.1039/C4OB01385A, PaperPavol Tisovsky, Maria Meciarova, Radovan Sebesta
The reactivity of aldehydes and ketones in asymmetric organo-SOMO reactions with enol silanes was explored. The best results were obtained with 3-phenylpropanal and tetralone-derived silyl enol ether and silyl ketene thioacetal.
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Transition metal-free oxidative esterification of benzylic alcohols in aqueous medium

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9453-9456
DOI: 10.1039/C4OB01524J, PaperSupravat Samanta, Venkatanarayana Pappula, Milan Dinda, Subbarayappa Adimurthy
Oxidative esterification of benzylic alcohols with catalytic HBr in aqueous medium under mild conditions is reported with a broad substrate scope including selective mono-esterification of ethylene glycol and glycerol.
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Conformationally locked bicyclo[4.3.0]nonane carbanucleosides: synthesis and bio-evaluation

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9439-9445
DOI: 10.1039/C4OB01763C, PaperTony K. M. Shing, Anthony W. H. Wong, Huiyan Li, Z. F. Liu, Paul K. S. Chan
D-Ribose was converted into 3 novel carbobicyclic nucleosides bearing a bicyclo[4.3.0]nonane framework in 16-19 steps with 5-12% overall yields involving a Wittig olefination and an intramolecular Diels-Alder reaction as the key steps.
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Revisiting the sparteine surrogate: development of a resolution route to the (-)-sparteine surrogate

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9357-9365
DOI: 10.1039/C4OB01694G, PaperJames D. Firth, Peter O'Brien, Leigh Ferris
A multi-gram scale, chromatography-free synthesis of the racemic sparteine surrogate and its resolution via diastereomeric salt formation with (-)-O,O[prime or minute]-di-p-toluoyl-L-tartaric acid is reported. This work solves a key limitation: either enantiomer of the sparteine surrogate can now be readily accessed.
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Rapid assembly of heterocycle grafted macrocycles via tandem one-pot double 1,3-dipolar cycloaddition reaction

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9375-9383
DOI: 10.1039/C4OB01778A, PaperR. Prasanna, S. Purushothaman, R. Raghunathan
Synthesis of triazole linked macrocycles grafted with glycospiroheterocycle was accomplished by stereo- and regioselective tandem double 1,3-dipolar cycloaddition (1,3-DC) reaction.
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Carbohydrates as a reagent in multicomponent reactions: one-pot access to a new library of hydrophilic substituted pyrimidine-fused heterocycles

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9419-9426
DOI: 10.1039/C4OB01791A, PaperMaryam Nourisefat, Farhad Panahi, Ali Khalafi-Nezhad
A new multicomponent reaction containing carbohydrates is developed for one-pot synthesis of a new class of hydrophilic substituted pyrimidine-fused heterocycles.
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Trienamines derived from 5-substituted furfurals: remote [varepsilon]-functionalization of 2,4-dienals

Org. and Biomol. Chem. - 11 November, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,9324-9328
DOI: 10.1039/C4OB01759E, CommunicationJaime A. S. Coelho, Alexandre F. Trindade, Vania Andre, M. Teresa Duarte, Luis F. Veiros, Carlos A. M. Afonso
The remote selective [varepsilon]-functionalization of 5-substituted furfurals by trienamine catalysis is described, resulting in a new scaffold.
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