Org. and Biomol. Chem.

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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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Diastereoselective synthesis of functionalized pyrrolidines through N-bromosuccinimide-induced aziridine ring expansion cascade of cinnamylaziridine

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7482-7485
DOI: 10.1039/C4OB01384K, CommunicationJing Zhou, Ying-Yeung Yeung
An efficient aziridine ring expansion cascade of cinnamylaziridine has been developed using N-bromosuccinimide as the promoter.
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A concise synthesis of (alkynyl)(trifluoromethyl)sulfanes via a bismuth(III)-promoted reaction of trimethyl(alkynyl)silane with trifluoromethanesulfanylamide

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7629-7633
DOI: 10.1039/C4OB01451K, PaperJie Sheng, Jie Wu
A bismuth(III)-promoted reaction of trimethyl(alkynyl)silanes with trifluoromethanesulfanylamide is developed, giving rise to (alkynyl)(trifluoromethyl)sulfanes in good yields.
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A new approach to asymmetric synthesis of infectocaryone

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7603-7611
DOI: 10.1039/C4OB01162G, PaperXiubing Liu, Lingling Hu, Xiaojing Liu, Junhao Jia, Lizhen Jiang, Jiangfeng Lin, Xiaochuan Chen
A new approach to the asymmetric synthesis of infectocaryone featuring a regioselective and stereoselective Diels-Alder reaction of an isomeric dienophile mixture is developed.
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Base-promoted dehydrogenative coupling of benzene derivatives with amides or ethers

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7469-7473
DOI: 10.1039/C4OB01253D, CommunicationRyota Ueno, Eiji Shirakawa
Electronically neutral and deficient benzene derivatives are introduced into the dehydrogenative coupling as arenes that couple with amides/ethers.
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Modular synthesis of bis- and tris-1,2,3-triazoles by permutable sequential azide-aryne and azide-alkyne cycloadditions

18 September, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,7489-7493
DOI: 10.1039/C4OB01654H, CommunicationSuguru Yoshida, Takako Nonaka, Takamoto Morita, Takamitsu Hosoya
A new method for aryne generation enabled facile synthesis of diverse bis- and tris-1,2,3-triazoles.
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Total synthesis and biological studies of cryptocin and derivatives of equisetin and fusarisetin A

16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7591-7597
DOI: 10.1039/C4OB01149J, PaperLili Kong, Mingjin Rao, Jinjie Ou, Jun Yin, Weiqiang Lu, Mingyao Liu, Xiufeng Pang, Shuanhu Gao
Total synthesis of cryptocin, derivatives of equisetin and fusarisetin A were achieved based on the biosynthetic hypothesis. The biological studies of their inhibitory effects on breast cancer cells (MDA-MB-231) survival and metastasis were further investigated.
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Understanding the polar mechanism of the ene reaction. A DFT study

16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7581-7590
DOI: 10.1039/C4OB01279H, PaperLuis R. Domingo, Maria J. Aurell, Patricia Perez
A good correlation between the activation energy and global electron density transfer at the transition structure of ene reactions has been found. The proposed polar mechanism can be easily predicted analysing the electrophilicity/nucleophilicity indices of the reagents.
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Modulation of DNA-polyamide interaction by [small beta]-alanine substitutions: a study of positional effects on binding affinity, kinetics and thermodynamics

16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7523-7536
DOI: 10.1039/C4OB01456A, PaperShuo Wang, Karl Aston, Kevin J. Koeller, G. Davis Harris, Nigam P. Rath, James K. Bashkin, W. David Wilson
The substitution of an internal pyrrole with a [small beta] motif has large and diverse effects on hairpin polyamide-DNA binding affinity, kinetics and binding orientation.
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Synthesis of aromatic 13C/2H-[small alpha]-ketoacid precursors to be used in selective phenylalanine and tyrosine protein labelling

16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7551-7560
DOI: 10.1039/C4OB01129E, PaperR. J. Lichtenecker
A synthetic concept to access various 13C/2H patterns of phenylalanine and tyrosine precursors for cell-based protein overexpression systems is presented. The target compounds feature isolated 13C-1H spin systems to be used in NMR probing of protein structure and dynamics.
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Nickel-catalyzed substitution reactions of propargyl halides with organotitanium reagents

16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7634-7642
DOI: 10.1039/C4OB00677A, PaperQing-Han Li, Jung-Wei Liao, Yi-Ling Huang, Ruei-Tang Chiang, Han-Mou Gau
A simple and mild catalytic coupling reaction of propargyl halides with organotitanium reagents is reported.
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Approaches to the total synthesis of chaetochalasin A

16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7537-7550
DOI: 10.1039/C4OB01308E, PaperEric J. Thomas, Mark Willis
Chaetochalasin A is a complex natural product whose biosynthesis may involve two domino Diels-Alder reactions.
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A theoretical study on the mechanisms of the reactions between 1,3-dialkynes and ammonia derivatives for the formation of five-membered N-heterocycles

16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7503-7514
DOI: 10.1039/C4OB01015A, PaperYang Wang, Donghui Wei, Wenjing Zhang, Yanyan Wang, Yanyan Zhu, Yu Jia, Mingsheng Tang
The reaction mechanisms between 1,3-dialkynes and ammonia derivatives for the formation of five-membered N-heterocycles have been investigated using the DFT method.
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