Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Stereoselective synthesis of 1,2-diamine containing indolines by a conjugate addition nitro-mannich reaction

7 December, 2014 - 20:17

Org. Biomol. Chem., 2015, 13,170-177
DOI: 10.1039/C4OB01793E, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.James C. Anderson, Ian B. Campbell, Sebastien Campos, Jonathan Shannon, Derek A. Tocher
The sequential use of the conjugate addition nitro-Mannich reaction, nitro reduction and then Pd-catalyzed intramolecular cyclisation allows the concise, stereodivergent synthesis of complex indolines.
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The stability of nitrogen-centered radicals

7 December, 2014 - 20:17

Org. Biomol. Chem., 2015, 13,157-169
DOI: 10.1039/C4OB01656D, PaperJohnny Hioe, Davor Sakic, Valerije Vrcek, Hendrik Zipse
Radical stabilization energies (RSEs) for a large variety of aminyl and protonated amine radical cations have been calculated using high-level composite procedures.
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Functional importance of the sugar moiety of jasmonic acid glucoside for bioactivity and target affinity

7 December, 2014 - 20:17

Org. Biomol. Chem., 2015, 13,55-58
DOI: 10.1039/C4OB02106A, CommunicationMinoru Ueda, Gangqiang Yang, Yuuki Nukadzuka, Yasuhiro Ishimaru, Satoru Tamura, Yoshiyuki Manabe
Importance of the D-glycopyranoside structure for the bioactivity and target affinity of jasmonic acid glucoside.
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Design and synthesis of potent hydroxamate inhibitors with increased selectivity within the gelatinase family

7 December, 2014 - 20:17

Org. Biomol. Chem., 2015, 13,142-156
DOI: 10.1039/C4OB01516A, PaperJose Maria Zapico, Anna Puckowska, Kamila Filipiak, Claire Coderch, Beatriz de Pascual-Teresa, Ana Ramos
Triazole-based inhibitors with high potency and selectivity for MMP-2 were obtained through a click chemistry approach.
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Ruthenium-catalyzed direct C3 alkylation of indoles with [small alpha],[small beta]-unsaturated ketones

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02124J, PaperShuai-Shuai Li, Hui Lin, Xiao-Mei Zhang, Lin Dong
In this paper, a simple and highly efficient ruthenium-catalyzed direct C3 alkylation of indoles with various [small alpha],[small beta]-unsaturated ketones without chelation assistance has been developed.
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Palladium-catalyzed oxidative cross-coupling of azole-4-carboxylates with indoles: an approach to the synthesis of pimprinine

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB01844C, PaperHaipin Zhou, Kuo Gai, Aijun Lin, Jinyi Xu, Xiaoming Wu, Hequan Yao
A palladium-catalyzed oxidative cross-coupling reaction between azole-4-carboxylates and indoles forming 5-(3-indolyl)azoles with excellent regioselectivity has been developed.
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Tunneling in tocopherol-mediated peroxidation of 7-dehydrocholesterol

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02377C, PaperH. Muchalski, L. Xu, N. A. Porter
We report here that H-atom tunneling facilitates the propagation step in the tocopherol-mediated peroxidation (TMP) of 7-dehydrocholesterol. This process likely becomes a major propagation pathway when radical intermediates are isolated in cellular organelles or lipid particles such as low-density lipoproteins. In TMP of 7-DHC and deuterium-reinforced 7-DHC, the KIE of removing hydrogen/deuterium at C9 was found to be 21 +/- 1.
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Characterizations of cationic [gamma]-carbolines binding with double-stranded DNA by spectroscopic methods and AFM imaging

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB01905A, PaperTao Jia, Jing Wang, Peng Guo, Junping Yu
Because of differences in their structures, cationic [gamma]-carbolines intercalate into DNA with different activities.
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Studies on the diastereoselective oxidation of 1-thio-[small beta]-D-glucopyranosides: Synthesis of the usually less favoured RS sulfoxide as a single diastereoisomer .

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02030H, PaperNoureddine Khiar, Juan Francisco Moya-Lopez, Eleonora Elhalem, Rocio Recio, Eleuterio Alvarez, Fernandez Inmaculada
Abstract: A detailed study on the diastereoselective oxidation of 1-thio--D-glucopyranosides is reported. It has been shown that the sense and the degree of stereochemical outcome of the oxidation is highly...
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A Chiral Borane Catalyzed Asymmetric Hydrosilylation of Imines

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02419B, CommunicationXiaxia Zhu, HAIFENG DU
An enantioselective hydrosilylation of imines was successfully achieved using a chiral borane catalyst generated by the in situ hydroboration of a binaphthyl-based chiral diene with Piers' borane HB(C6F5)2 to furnish...
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A case of oxoanion recognition based on combined cationic and neutral C-H hydrogen bond interactions

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02288B, PaperFabiola Zapata, Paula Sabater, Antonio Caballero, Pedro Molina
A bidentate bis-(benzimidazolium) receptor containing pyrene as fluorescent signaling units recognizes sulphate and hydrogenpyrophosphate in a competitive water-DMSO medium through combinations of cationic and neutral C-H hydrogen bonding.
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Metal-catalyzed formation of 1,3-cyclohexadienes: a catalyst-dependent reaction

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB01922A, PaperShifa Zhu, Xiaobing Huang, Tian-Qi Zhao, Tongmei Ma, Huanfeng Jiang
A metal-dependent and complementary catalytic method to synthesize the cyclohexadienes has been developed. When gold or indium salts were used as catalysts, 1,3-cyclohexadiene (1,3-CHD) could be obtained; when Cu(OTf)2 was used as the catalyst, however, another isomer 2,4-cyclohexadiene (2,4-CHD) was furnished instead.
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N-Heterocyclic Carbene-Catalyzed Cyclocondensation of 2-Aryl Carboxylic Acid and Enones: Highly Enantioselective Synthesis of [small delta]-Lactones

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02330G, CommunicationJin-Tang Cheng, Xiang-Yu Chen, Song Ye
The enantioselective N-heterocyclic carbene-catalyzed [4 + 2] cyclocondensation of 2-aryl carboxylic acids and enones was developed, affording the corresponding chiral [small delta]-lactones in good yields with good diastereo- and high enantioselectivities.
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Fluorescent organic nanoparticles of dihydropyrimidone derivatives for selective recognition of iodide using a displacement assay: application of the sensors in water and biological fluids

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02152E, PaperAmanpreet Kaur, Tilak Raj, Simanpreet Kaur, Narinder Singh, Navneet Kaur
Fluorescent organic nanoparticles (FON's) derived from dihydropyrimidone derivatives (1-4) were developed and evaluated for their sensor properties.
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Stereodivergent Synthesis of the LFA-1 Antagonist BIRT 377 by Porcine Liver Esterase Desymmetrization and Curtius Rearrangement

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02303J, PaperThomas G Back, Aaron Johnson, Matthew J. Saunders
The LFA-1 inhibitor and leukocyte adhesion suppressor BIRT-377 was prepared in high enantiomeric excess by desymmetrization of dimethyl 2-p-bromobenzyl-2-methylmalonate, followed by condensation of the resulting carboxylic acid with 3,5-dichloroaniline, saponification...
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Synthesis, and QSAR analysis of anti-oncological active spiro-alkaloids

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02149E, PaperAS Girgis, Siva S Panda, I. S. Ahmed Farag, A. M. El-Shabiny, A. M. Moustafa, nasser saad ismail, Girinath G. Pillai, Chandramukhi S. Panda, Charles Dennis Hall, Alan R Katritzky
QSAR study describes the anti-neoplastic spiro-alkaloids with relevant molecular descriptors using CODESSA III software. The dispiro[3H-indole-3,2'-pyrrolidine-3',3''-piperidines] 24-48 were synthesized via [3+2]-cycloaddition reaction of azomethine ylides, (generated in situ via decarboxylative...
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Synthesis of N-Glycolyl Muramyl Dipeptide

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02147A, PaperShuo Xing, James L Gleason
A novel synthetic route leading to N-glycolyl muramyl dipeptide (MDP), a bacterial glycopeptide of particular interest in studies of nucleotide-binding oligomerization domain-containing protein 2 (NOD2), is described. The synthetic strategy...
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Consecutive three-component synthesis of (hetero)arylated propargyl amides by chemoenzymatic aminolysis-Sonogashira coupling sequence

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02386B, PaperSidra Hassan, Anja Ullrich, Thomas J.J. Mueller
A novel chemoenzymatic three-component synthesis of (hetero)arylated propargyl amides in good yields based upon Novozyme[registered sign] 435 (Candida antarctica lipase B (CAL-B)) catalyzed aminolysis of methyl carboxylates followed by Sonogashira coupling...
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Sugar-Derived Amine Catalyzed Intramolecular Diels-Alder Reactions

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02219J, PaperTony K. M. SHING, Kwun W. Wu, Ho T Wu, Qicai Xiao
Six chiral hydroxylated pyrrolidine catalysts were synthesized from commercially available D-arabinose in seven steps. Various aromatic substituents [small alpha] to the amine can be introduced readily by a Grignard reaction, which...
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Probing coiled-coil assembly by paramagnetic NMR spectroscopy

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02125H, PaperTingTing Zheng, Aimee Boyle, Hana Robson Marsden, Dayenne Valdink, Giuliana Martelli, Jan Raap, Alexander Kros
Here a new method to determine the orientation of coiled-coil peptide motifs is described.
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