Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Synthesis of tetracyclic chromenones via platinum(II) chloride catalysed cascade cyclization of enediyne-enones

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1318-1327
DOI: 10.1039/C3OB41911H, PaperMahalingam Sivaraman, Paramasivan T. Perumal
PtCl2 catalysed cascade cyclization of an enediyne-enone system to afford naphthalene fused chromenones in good to excellent yield and attempts to synthesize chrysene fused chromenone are reported in this manuscript.
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Nickel-catalyzed triarylamine synthesis: synthetic and mechanistic aspects

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1232-1236
DOI: 10.1039/C3OB42053A, PaperXin-Le Li, Wei Wu, Xin-Heng Fan, Lian-Ming Yang
Triarylamine was synthesised from nickel-catalyzed amination, and the reaction mechanism of a NiI-NiIII cycle is proposed.
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Yellow NIR dye: [small pi]-fused bisbenzoBODIPYs with electron-withdrawing groups

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1309-1317
DOI: 10.1039/C3OB41996G, PaperMitsunori Nakamura, Manami Kitatsuka, Kohtaro Takahashi, Toshi Nagata, Shigeki Mori, Daiki Kuzuhara, Tetsuo Okujima, Hiroko Yamada, Takahiro Nakae, Hidemitsu Uno
Stable benzene-fused bisbenzoBODIPY with four cyano groups is ideal for a NIR-selective dye, which shows strong absorption in the NIR region and good transparency in the visible region.
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Huisgen-based conjugation of water-soluble porphyrins to deprotected sugars: towards mild strategies for the labelling of glycans

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1203-1206
DOI: 10.1039/C3OB42306A, CommunicationFrancesca Giuntini, Francesca Bryden, Robin Daly, Eoin M. Scanlan, Ross W. Boyle
Fully deprotected alkynyl-functionalised mono- and oligosaccharides undergo CuAAC-based conjugation with water-soluble porphyrin azides in aqueous environments.
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Investigation of quantitative structure-reactivity relationships in the aliphatic Claisen rearrangement of bis-vinyl ethers reveals a dipolar, dissociative mechanism

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1292-1308
DOI: 10.1039/C3OB42011F, PaperNatasha F. O'Rourke, Jeremy E. Wulff
Kinetic investigations of substituent effects in the Claisen rearrangement of bis-vinyl ether substrates suggest a dissociative mechanism of reaction.
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NH-type of chiral Ni(II) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1278-1291
DOI: 10.1039/C3OB41959B, PaperMackenzie Bergagnini, Kazunobu Fukushi, Jianlin Han, Norio Shibata, Christian Roussel, Trevor K. Ellis, Jose Luis Acena, Vadim A. Soloshonok
Readily available "N-H"-type of Ni(II) complexes derived from glycine undergo highly diastereoselective alkylation and Michael addition reactions, as a convenient method for the synthesis of amino acids.
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NBS mediated nitriles synthesis through C[double bond, length as m-dash]C double bond cleavage

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1198-1202
DOI: 10.1039/C3OB42118J, CommunicationXiaolin Zong, Qing-Zhong Zheng, Ning Jiao
An NBS mediated nitrile synthesis through C[double bond, length as m-dash]C double bond cleavage has been developed.
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Organocatalysed synthesis of isoxazolines initiated by a chemoselective oxa-Michael reaction of N-BocNHOH

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1245-1249
DOI: 10.1039/C3OB42406E, PaperR. Noel, V. Gembus, V. Levacher, J.-F. Briere
An organocatalysed and chemoselective one-pot oxa-Michael-cyclocondensation reaction of N-BocNHOH to unsaturated [small alpha]-ketoesters is reported which affords an original entry to enantioenriched 3-isoxazoline carboxylate derivatives as biorelevant heterocyclic frameworks.
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Organocatalytic enantioselective hydrophosphonylation of aldehydes

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1258-1264
DOI: 10.1039/C3OB42403K, PaperJuan V. Alegre-Requena, Eugenia Marques-Lopez, Pablo J. Sanz Miguel, Raquel P. Herrera
We report our results concerning the first squaramide-catalysed hydrophosphonylation of aldehydes.
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Synthesis of macrolactam analogues of radicicol and their binding to heat shock protein Hsp90

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1328-1340
DOI: 10.1039/C3OB42211A, PaperBridie L. Dutton, Russell R. A. Kitson, Sarah Parry-Morris, S. Mark Roe, Chrisostomos Prodromou, Christopher J. Moody
Macrolactam analogues of the natural lactone radicicol bind to Hsp90.
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Liposome surface functionalization based on different anchoring lipids via Staudinger ligation

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1237-1244
DOI: 10.1039/C3OB41721B, PaperPratima Vabbilisetty, Xue-Long Sun
Glyco-functionalized liposome systems based on two kinds of anchoring lipids were prepared and studied for stability, encapsulation and releasing capacity of the liposomes and accessibility of their grafted carbohydrate residues.
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An ebselen like catalyst with enhanced GPx activity via a selenol intermediate

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1215-1219
DOI: 10.1039/C4OB00027G, CommunicationShah Jaimin Balkrishna, Shailesh Kumar, Gajendra Kumar Azad, Bhagat Singh Bhakuni, Piyush Panini, Navjeet Ahalawat, Raghuvir Singh Tomar, Michael R. Detty, Sangit Kumar
Benzamide ring-substituted, quinine-derived ebselen analogue is synthesized which exists in selenol form upon addition of PhSH. It catalyses oxidation of PhSH with H2O2 faster (103-fold) than ebselen.
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Synthesis, biophysical studies and RNA interference activity of RNA having three consecutive amide linkages

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1207-1210
DOI: 10.1039/C3OB42532K, CommunicationPaul Tanui, Scott D. Kennedy, Benjamin D. Lunstad, Amanda Haas, Devin Leake, Eriks Rozners
RNA sequences having up to three consecutive internal amide linkages were synthesized and studied using UV and NMR spectroscopy and RNA interference activity assays.
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Modulating glycosylation with exogenous nucleophiles: an overview

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1184-1197
DOI: 10.1039/C3OB42129E, Review ArticleShaheen K. Mulani, Wei-Cheng Hung, Arun B. Ingle, Kai-Sheng Shiau, Kwok-Kong Tony Mong
Control of stereochemistry in glycosidic bond formation through exogenous nucleophiles.
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Theoretical investigations toward the tandem reactions of N-aziridinyl imine compounds forming triquinanes via trimethylenemethane diyls: mechanisms and stereoselectivity

11 February, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,1220-1231
DOI: 10.1039/C3OB42115E, PaperYan Qiao, Ke-Li Han
A theoretical study on the mechanism and stereoselectivity of tandem reactions of N-aziridinyl imine compounds forming triquinanes via trimethylenemethane diyls.
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Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation of (Z)-[small alpha]-santalol

3 February, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,1048-1051
DOI: 10.1039/C3OB42174K, CommunicationPankaj P. Daramwar, Prabhakar Lal Srivastava, Swati P. Kolet, Hirekodathakallu V. Thulasiram
Biocatalyst mediated regio- and stereo-selective functionalization of (Z)-[small alpha]-santalol using a highly efficient fungal system M. piriformis furnished four novel metabolites, characterized for the first time. Kinetic resolution of 10,11-epoxy-[small alpha]-santalols was accomplished using Amano lipase PS from B. cepacia.
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Site-selected incorporation of 5-carboxymethylaminomethyl(-2-thio)uridine into RNA sequences by phosphoramidite chemistry

3 February, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,1052-1056
DOI: 10.1039/C3OB42302F, CommunicationGrazyna Leszczynska, Jakub Pieta, Karolina Wozniak, Andrzej Malkiewicz
This study presents the first site-selected incorporation of cmnm5U and cmnm5s2U into RNA sequences by phosphoramidite chemistry on a CPG support.
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Rhodium-catalyzed three-component reaction of 3-diazooxindoles with indoles and isatin-derived ketimines: a facile and versatile approach to functionalized 3,3[prime or minute],3[prime or minute][prime or minute]-trisindoles

3 February, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,1149-1156
DOI: 10.1039/C3OB42283F, PaperLiang-Yong Mei, Xiang-Ying Tang, Min Shi
A variety of functionalized 3,3[prime or minute],3[prime or minute][prime or minute]-trisindoles could be produced in high yields with moderate to excellent diastereoselectivities via Rh2(OAc)4-catalyzed three-component reaction of 3-diazooxindoles with indoles and isatin-derived N-Boc ketimines.
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Synthesis of bicyclic organo-peptide hybrids via oxime/intein-mediated macrocyclization followed by disulfide bond formation

3 February, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,1135-1142
DOI: 10.1039/C3OB42222D, PaperJessica M. Smith, Nicholas C. Hill, Peter J. Krasniak, Rudi Fasan
A new strategy is described to convert recombinant polypeptides into bicyclic organo-peptide hybrids constrained by an intramolecular disulfide bridge.
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KI-catalyzed arylation of benzothiazoles from the coupling of aryl aldehydes with benzothiazoles in neat water

3 February, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,1044-1047
DOI: 10.1039/C3OB42318B, CommunicationYuyu Gao, Qiuling Song, Guolin Cheng, Xiuling Cui
A KI-catalyzed oxidative coupling of benzothiazoles with aryl aldehydes using TBHP as an oxidant in neat water under metal free conditions is described.
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