Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Robust asymmetric synthesis of unnatural alkenyl amino acids for conformationally constrained [small alpha]-helix peptides

22 October, 2014 - 08:54

Org. Biomol. Chem., 2014, 12,8775-8782
DOI: 10.1039/C4OB01832J, PaperBoris Aillard, Naomi S. Robertson, Adam R. Baldwin, Siobhan Robins, Andrew G. Jamieson
The efficient asymmetric synthesis of unnatural alkenyl amino acids required for peptide 'stapling' has been achieved using alkylation of a fluorine-modified NiII Schiff base complex as the key step.
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Rhodium-catalyzed ortho-cyanation of symmetrical azobenzenes with N-cyano-N-phenyl-p-toluenesulfonamide

22 October, 2014 - 08:54

Org. Biomol. Chem., 2014, 12,8603-8606
DOI: 10.1039/C4OB01736F, CommunicationJie Han, Changduo Pan, Xuefeng Jia, Chengjian Zhu
A rhodium(III)-catalyzed ortho-cyanation of symmetrical azobenzenes with NCTS via azo-group-directed C(sp2)-H bond activation is described.
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Enantioselective synthesis of 3-substituted 1,2-oxazinanes via organocatalytic intramolecular aza-Michael addition

22 October, 2014 - 08:54

Org. Biomol. Chem., 2014, 12,8607-8610
DOI: 10.1039/C4OB01646G, CommunicationShuanghua Cheng, Shouyun Yu
A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er).
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Preparation of indium nitronates and their Henry reactions

22 October, 2014 - 08:54

Org. Biomol. Chem., 2014, 12,8593-8597
DOI: 10.1039/C4OB01468E, CommunicationRaquel G. Soengas, Rita Acurcio, Artur M. S. Silva
Indium nitronates were readily prepared from commercially available nitroalkanes by transmetallation of the corresponding lithium nitronates with indium salts. The Henry reaction of this nitronates with aldehydes afforded [small beta]-nitroalkanols in moderate to high yields and excellent stereoselectivity (when using chiral aldehydes).
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Anti-hepatitis B virus activities and absolute configurations of sesquiterpenoid glycosides from Phyllanthus emblica

22 October, 2014 - 08:54

Org. Biomol. Chem., 2014, 12,8764-8774
DOI: 10.1039/C4OB01196A, PaperJun-Jiang Lv, Ya-Feng Wang, Jing-Min Zhang, Shan Yu, Dong Wang, Hong-Tao Zhu, Rong-Rong Cheng, Chong-Ren Yang, Min Xu, Ying-Jun Zhang
The sesquiterpenoid glycoside dimers isolated from Phyllanthus emblica have anti-HBV activities towards HBsAg and HBeAg secretions inhibition.
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A metal-free one-pot cascade synthesis of highly functionalized biaryl-2-carbaldehydes

22 October, 2014 - 08:54

Org. Biomol. Chem., 2014, 12,8588-8592
DOI: 10.1039/C4OB01829J, CommunicationChandrasekhar Challa, Jamsheena Vellekkatt, Jaice Ravindran, Ravi S. Lankalapalli
A metal-free one-pot cascade annulation of acyclic substrates dienaminodioate, cinnamaldehydes and allyl amine was achieved for the synthesis of polyfunctional biaryl-2-carbaldehydes.
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Cross-strand histidine-aromatic interactions enhance acyl-transfer rates in beta-hairpin peptide catalysts

22 October, 2014 - 08:54

Org. Biomol. Chem., 2014, 12,8711-8718
DOI: 10.1039/C4OB01754D, PaperM. Matsumoto, S. J. Lee, M. R. Gagne, M. L. Waters
A His-aryl interaction in a beta-hairpin catalyst provides rate enhancements of up to 18 000 for acyl transfer catalysis.
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Highly enantioselective phosphination and hydrophosphonylation of azomethine imines: using chiral squaramide as a hydrogen bonding organocatalyst

22 October, 2014 - 08:54

Org. Biomol. Chem., 2014, 12,8656-8670
DOI: 10.1039/C4OB01472C, PaperLing-Pei Kong, Nai-Kai Li, Shao-Yun Zhang, Xiang Chen, Min Zhao, Ya-Fei Zhang, Xing-Wang Wang
Highly enantioselective phosphination and hydrophosphonylation reactions of azomethine imines are respectively reported in this paper.
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Synthesis of PS/PO-Chimeric Oligonucleotides Using Mixed Oxathiaphospholane and Phosphoramidite Chemistry

20 October, 2014 - 08:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01837K, PaperJanina Baraniak, Ewa Radzikowska
Chimeric oligonucleotides containing phosphodiester and phosphorothioate linkages have been obtained using the solid phase synthesis. The oligonucleotide parts possessing natural internucleotide phosphate bonds were assembled using commercially available nucleoside 3'-O-(2-cyanoethyl-N,N-diisopropylamino)phosphoramidites...
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Construction of Dispirocyclohexanes via Amine-Catalyzed [2 + 2 + 2] Annulations of Morita-Baylis-Hillman Acetates with Exocyclic Alkenes

20 October, 2014 - 08:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01927J, PaperRongshun Chen, Silong Xu, Xia Fan, Hanyuan Li, Yuhai Tang, Zhengjie He
Amine-catalyzed [2 + 2 + 2] annulations of one molecule of Morita-Baylis-Hillman (MBH) acetates 1 with two molecules of 2-(arylmethylidene)indane-1,3-diones 2 or methyleneindolinones 4 have been developed under very mild...
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Novel naphthoquinone derivatives and evaluation of trypanocidal and leishmanicidal activities

20 October, 2014 - 08:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01869A, PaperDenis Pires de Lima, Aline Alves dos Santos Naujorks, Adriano O da Silva, Rosangela S Lopes, Sergio de Albuquerque, Adilson Beatriz, Maria Rita Marques
Herein it is reported the synthesis of 12 new naphthoquinone derivatives, comprising 6 substituted 1,4-naphthoquinones and 6 heterocycle-fused naphthoquinones, as well as the evaluation of their trypanocidal and leishmanicidal activities....
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Synthesis of novel symmetrical 2-oxo-spiro[indole-3,4'-pyridines] by reaction of oxindoles with 1,2-diaza-1,3-dienes

20 October, 2014 - 08:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01959H, PaperFabio Mantellini, O A Attanasi, Lucia De Crescentini, Gianfranco Favi, Linda Antonella Campisi
A simple reaction of some oxindole derivatives with 1,2-diaza-1,3-dienes to produce 2-oxo-spiro[indole-3,4'-pyridines] in good yields is here described. This transformation represents a practical two steps approach to new and biologically...
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Biomineralization-inspired synthesis of functional organic/inorganic hybrid materials: organic molecular control of self-organization of hybrids

20 October, 2014 - 08:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01796J, Review ArticleAtushi Arakaki, Katsuhiko Shimizu, Mayumi Oda, Takeshi Sakamoto, Tatsuya Nishimura, Takashi Kato
Organisms produce various organic/inorganic hybrid materials, which are called biominerals. They form through the self-organization of organic molecules and inorganic elements under ambient conditions. Biominerals often show highly organized and...
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Bidirectional Macrocyclization of Peptides by Double Multicomponent Reaction

20 October, 2014 - 08:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01915F, PaperManuel G Ricardo, Fidel E Morales, Hilda Garay, Osvaldo Reyes, Dimitar Vasilev, Ludger A. Wessjohann, Daniel G. Rivera
Increasing the diversity of peptide cyclization methods is an effective way to access new types of macrocyclic chemotypes featuring a wide variety of ring sizes and topologies. Multicomponent reactions (MCRs)...
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An efficient synthetic route to 1,3-bis(arylethynyl)isobenzofuran by using alkoxybenzocyclobutenone as a reactive platform

20 October, 2014 - 08:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02012J, CommunicationToshiyuki Hamura, Kenta Asahina, Suguru Matsuoka, Ryosuke Nakayama
An efficient synthetic method of 1,3-bis(arylethynyl)isobenzofurans has been developed. Nucleophilic addition of alkynyllithium to benzocyclobutenone and subsequent oxidative ring cleavage of the four-membered ring gave keto-aldehyde, which, in turn, accepted...
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Selective Oxygenation of Alkynes: A Direct Approach to Diketones and Vinyl Acetate

20 October, 2014 - 08:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01404A, PaperXiao-Feng Xia, Zhen Gu, Wentao Liu, Ningning Wang, Haijun Wang, yong-mei Xia, Haiyan Gao, Xiang Liu
Arylalkynes can convert into [small alpha]-diketones by the use of copper catalyst, and also transform into vinyl acetates under metal-free conditions both in the presence of PhI(OAc)2 as oxidant at room...
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Biosynthesis of 8-hydroxyquinoline-2-carboxylic acid, an iron chelator from the gut of the lepidopteran Spodoptera littoralis

20 October, 2014 - 08:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01857E, PaperJelena Pesek, Jiri Svoboda, Martina Sattler, Stefan Bartram, Wilhelm Boland
In the regurgitate (foregut content) of Spodoptera larvae we found high concentrations (0.5 - 5 mM) of 8-hydroxyquinoline-2-carboxylic acid (8-HQA). In a survey of different lepidopteran species, this compound was...
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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

20 October, 2014 - 08:17

Org. Biomol. Chem., 2014, Advance Article
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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A review of methods to synthesise 4[prime or minute]-substituted nucleosides

20 October, 2014 - 08:17

Org. Biomol. Chem., 2014, Advance Article
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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Revisiting the sparteine surrogate: development of a resolution route to the (-)-sparteine surrogate

20 October, 2014 - 08:17

Org. Biomol. Chem., 2014, Advance Article
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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