Org. and Biomol. Chem.

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Oxenoids in organic synthesis

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1535-1546
DOI: 10.1039/C3OB42349B, Review ArticleYury Minko, Ilan Marek
Recent advances on the use of oxenoid compounds in organic synthesis are highlighted in this review.
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Synthesis of benzannulated heterocycles by twofold Suzuki-Miyaura couplings of cyclic diarylborinic acids

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1391-1394
DOI: 10.1039/C3OB42065E, CommunicationElena Dimitrijevic, Madeline Cusimano, Mark S. Taylor
Successive transmetallations of the two C-B bonds of cyclic borinic acids enable a novel synthesis of benzo-fused heterocycles from readily available precursors.
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Syntheses and photophysical properties of BF2 complexes of curcumin analogues

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1618-1626
DOI: 10.1039/C3OB42201A, PaperGuifeng Bai, Changjiang Yu, Chi Cheng, Erhong Hao, Yun Wei, Xiaolong Mu, Lijuan Jiao
Highly photostable [small pi]-extended curcumin-BF2 complexes with strong absorption and fluorescence ranging from 400 to 800 nm were reported.
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Two-dimensional self-assembly of amphiphilic porphyrins on a dynamically shrinking droplet surface

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1627-1632
DOI: 10.1039/C3OB41723A, PaperMunenori Numata, Yusuke Takigami, Naoya Hirose, Ryoichiro Sakai
Unique self-assembled structures can be selectively created depending on the initial stage of the droplet. By using the droplet as a self-assembly field, we can select an appropriate self-assembly pathway by merely changing the initial state of the droplet.
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A remarkable regiocontrol in the palladium-catalyzed silylstannylation of fluoroalkylated alkynes - highly regio- and stereoselective synthesis of multi-substituted fluorine-containing alkenes

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1611-1617
DOI: 10.1039/C3OB41903G, PaperTsutomu Konno, Ryoko Kinugawa, Takashi Ishihara, Shigeyuki Yamada
The palladium-catalyzed silylstannylation reaction of CF3-containing alkynes proceeded very smoothly to give the corresponding adducts in a highly cis-selective manner. In this reaction, a novel regiocontrol by switching the palladium catalyst was observed.
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First example of quinine-squaramide catalyzed enantioselective addition of diphenyl phosphite to ketimines derived from isatins

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1595-1602
DOI: 10.1039/C3OB42026D, PaperJimil George, B. Sridhar, B. V. Subba Reddy
A quinine-squaramide catalyzed asymmetric addition of diphenyl phosphite to isatin derived ketimines is reported.
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Chiral squaramide-catalysed one-pot enantioselective sulfa-Michael addition/thioesterification of thiols with [small alpha],[small beta]-unsaturated N-acylated succinimides

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1585-1594
DOI: 10.1039/C3OB42137F, PaperBo-Liang Zhao, Da-Ming Du
A novel enantioselective one-pot dithiolation through sulfa-Michael addition/thioesterification of thiols with [small alpha],[small beta]-unsaturated N-acylated succinimides catalysed by squaramide afforded [small beta]-sulfated thioesters in good to excellent yields with high enantioselectivities (up to 96% ee).
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Identification and optimization of short helical peptides with novel reactive functionality as catalysts for acyl transfer by reactive tagging

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1488-1494
DOI: 10.1039/C3OB41421C, PaperSilvia Bezer, Masaomi Matsumoto, Michael W. Lodewyk, Stephen J. Lee, Dean J. Tantillo, Michel R. Gagne, Marcey L. Waters
A high-throughput screening method is used for identification of new catalytic functionalities for transesterification reaction in organic solvent.
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Live cell cytoplasm staining and selective labeling of intracellular proteins by non-toxic cell-permeant thiophene fluorophores

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1603-1610
DOI: 10.1039/C3OB41982G, PaperF. Di Maria, I. E. Palama, M. Baroncini, A. Barbieri, A. Bongini, R. Bizzarri, G. Gigli, G. Barbarella
Newly synthesized cell-permeant thiophene fluorophores experience a distinct fate inside live cells: from cytoplasm staining to selective tagging of globular proteins.
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Callyspongisines A-D: bromopyrrole alkaloids from an Australian marine sponge, Callyspongia sp.

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1579-1584
DOI: 10.1039/C4OB00091A, PaperFabien Plisson, Pritesh Prasad, Xue Xiao, Andrew M. Piggott, Xiao-cong Huang, Zeinab Khalil, Robert J. Capon
An Australian Callyspongia sp. yielded the new bromopyrrole alkaloids callyspongisines A-D. Callyspongisine A is only the second reported example of a natural imino-oxazoline and the first to feature a spiro heterocyclic framework.
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Synthesis of full length and truncated microcin B17 analogues as DNA gyrase poisons

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1570-1578
DOI: 10.1039/C3OB42516A, PaperRobert E. Thompson, Frederic Collin, Anthony Maxwell, Katrina A. Jolliffe, Richard J. Payne
Using a combination of solid-phase peptide synthesis and fragment assembly strategies a library of full-length and truncated analogues of the antibacterial post-translationally modified peptide microcin B17 have been synthesised. Both antibacterial and DNA gyrase poisoning activities are also described for the synthetic analogues.
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Synthesis, structure and inhibitory activity of a stereoisomer of oseltamivir carboxylate

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1561-1569
DOI: 10.1039/C3OB42069H, PaperAndrea Sartori, Luca Dell'Amico, Lucia Battistini, Claudio Curti, Silvia Rivara, Daniele Pala, Philip S. Kerry, Giorgio Pelosi, Giovanni Casiraghi, Gloria Rassu, Franca Zanardi
A versatile asymmetric synthesis of the C-4 epimer of oseltamivir carboxylate (OC) is reported. A marked drop in inhibitory activity toward influenza virus neuraminidase was observed and rationalized.
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Identification of BP16 as a non-toxic cell-penetrating peptide with highly efficient drug delivery properties

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1652-1663
DOI: 10.1039/C3OB42422G, PaperMarta Soler, Marta Gonzalez-Bartulos, David Soriano-Castell, Xavi Ribas, Miquel Costas, Francesc Tebar, Anna Massaguer, Lidia Feliu, Marta Planas
BP16 is a non-toxic cell-penetrating peptide with high cellular uptake in vitro. This peptide is an efficient vector for the delivery of therapeutic agents into cells, as has been shown for the anticancer drug chlorambucil.
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Ring contraction of 1,3-diphenylbenzo[1,2,4]triazinyl radicals to 1,2-diphenylbenzimidazoles

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1641-1648
DOI: 10.1039/C3OB42130A, PaperAndrey A. Berezin, Panayiotis A. Koutentis
Optimized conditions for the reductive ring contraction of benzotriazinyl radicals and related analogues afford benzimidazoles in near quantitative yields.
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Synthesis of substituted 3-furanoates from MBH-acetates of acetylenic aldehydes via tandem isomerization-deacetylation-cycloisomerization: access to Elliott's alcohol

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1664-1670
DOI: 10.1039/C3OB42396D, PaperChada Raji Reddy, Gaddam Krishna, Motatipally Damoder Reddy
A new approach for the synthesis of 5-substituted 3-furoates from MBH-acetates of acetylenic aldehydes has been developed. This methodology provided an entry to Elliott's alcohol, a key subunit of resmethrin.
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Chemoselective and repetitive intermolecular cross-acyloin condensation reactions between a variety of aromatic and aliphatic aldehydes using a robust N-heterocyclic carbene catalyst

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1547-1550
DOI: 10.1039/C3OB42486C, CommunicationMing Yu Jin, Sun Min Kim, Hui Mao, Do Hyun Ryu, Choong Eui Song, Jung Woon Yang
Chemoselectivity of the crossed acyloin product is controlled by the adjustment of the aromatic aldehyde/aliphatic aldehyde ratio.
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A rapid and efficient access to renieramycin-type alkaloids featuring a temperature-dependent stereoselective cyclization

25 February, 2014 - 23:17

Org. Biomol. Chem., 2014, 12,1633-1640
DOI: 10.1039/C3OB42209G, PaperHao Liu, Ruijiao Chen, Xiaochuan Chen
A flexible protocol for the asymmetric syntheses of renieramycin-type alkaloids featuring a temperature-dependent Pictet-Spengler cyclization and the subsequent lactamization is described.
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A fluorene-based material containing triple azacrown ether groups: synthesis, characterization and application in chemosensors and electroluminescent devices

19 February, 2014 - 21:54

Org. Biomol. Chem., 2014, 12,1419-1429
DOI: 10.1039/C3OB42054J, PaperChia-Shing Wu, Ying-Ju Lin, Yun Chen
A novel fluorene-based FTC containing triple azacrown ether groups is applied as a chemical sensor and as an electron injection layer simultaneously.
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NMR elucidation of the role of Mg2+ in the structure and stability of the conserved RNA motifs of the EMCV IRES element

19 February, 2014 - 21:54

Org. Biomol. Chem., 2014, 12,1495-1509
DOI: 10.1039/C3OB41840E, PaperSadia Mohammed, Marie M. Phelan, Usman Rasul, Vasudevan Ramesh
NMR structure of the highly conserved and functionally significant 16mer RNA motif endowed with a classic "GNRA" tetraloop of the novel EMCV IRES element.
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Deproto-metallation using a mixed lithium-zinc base and computed CH acidity of 1-aryl 1H-benzotriazoles and 1-aryl 1H-indazoles

19 February, 2014 - 21:54

Org. Biomol. Chem., 2014, 12,1475-1487
DOI: 10.1039/C3OB42380H, PaperElisabeth Nagaradja, Floris Chevallier, Thierry Roisnel, Vincent Dorcet, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Florence Mongin
1-Aryl-1H-benzotriazoles have been deproto-metallated using a 2,2,6,6-tetramethylpiperidino-based Li-Zn combination. The regioselectivity has been discussed in the light of DFT-calculated CH acidities (THF solution).
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