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The asymmetric syntheses of pyrrolizidines, indolizidines and quinolizidines via two sequential tandem ring-closure/N-debenzylation processes

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01737D, PaperStephen G. Davies, Ai M Fletcher, Emma Foster, Ian Houlsby, Paul Roberts, Thomas Schofield, James E. Thomson
Concise asymmetric syntheses of (-)-lupinine, (+)-isoretronecanol, (+)-5-epi-tashiromine and (R,R)-1-(hydroxymethyl)octahydroindolizine (the azabicyclic core within stellettamides A-C), have been achieved in 8 steps or fewer from commercially available starting materials. The key...
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Thermodynamic epimeric equilibration and crystallisation-induced dynamic resolution of lobelanine, norlobelanine and related analogues

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01787K, PaperZacharias Amara, Guillaume Bernadat, Pierre-Etienne Venot, Pascal Retailleau, Claire Troufflard, Emmanuelle Drege, Franck LE BIDEAU, Delphine Joseph
The step-economical synthesis of lobelanine implying a ring closing double aza-Michael (RCDAM) reaction is revisited and successfully extended to the synthesis of various configurationally more stable analogues. Owing to the...
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One Molecule of Ionic Liquid and tert-Alcohol on Polystyrene-Support as Catalysts for Efficient Nucleophilic Substitution Including Fluorination

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01781A, PaperSANDIP S SHINDE, Sunil N Patil
The tert-alcohol and ionic liquid solvents in one molecule ([mim-tOH][OMs], Fig 1) was immobilized on polystyrene reported to be a highly efficient catalyst in aliphatic nucleophilic substitution using alkali metal...
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Synthesis of functionalized fulvenes: [3+2] annulation of ethyl [small alpha]-chlorocyclopropaneformates with 1, 3-dicarbonyl compounds

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01973C, CommunicationYuefa gong, Yuequan Zhu, Min Zhang, Hongling Yuan
A base-promoted [3+2] annulation reaction of ethyl [small alpha]-chlorocyclopropaneformates with 1,3 -dicarbonyl compounds was described. This method provides an efficient straightforward route to acidic multi-substituted fulvenes with distinctive properties in contrast...
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Carbohydrates as reagent in multicomponent reaction: One-pot access to a new library of hydrophilic substituted pyrimidine-fused heterocycles

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01791A, PaperMaryam Nourisefat, Farhad Panahi, Ali Khalafi-Nezhad
In this study a multicomponent reaction involving carbohydrate derivatives as main component in order to prepare a new library of polyhydroxy compounds incorporating pyrimidine-fused heterocycles (PFHs) is introduced. A set...
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Metal-free, one-pot conversion of proline derivatives into 2-ary-3-iodo pyrrolidines, by a sequential scission-iodination-arylation process

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01372G, PaperAlicia Boto, Ivan Romero-Estudillo, Venkateswara Rao Batchu, Javier Miguelez
The metal-free, direct conversion of readily available proline derivatives into 2-aryl-3-iodopyrrolidines is carried out under mild conditions and good yields, using a sequential radical decarboxylation-oxidation-iodination-arylation reaction. These iodinated pyrrolidines are...
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Trienamines derived from 5-substituted furfurals: remote [varepsilon]-functionalization of 2,4-dienals

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01759E, CommunicationCarlos A. M. Afonso, Jaime A. S. Coelho, Alexandre Trindade, Vania Andre, Maria Teresa Duarte, Luis F. Veiros
The selective [varepsilon] functionalization of 5-substituted furfurals via trienamine intermediates is reported. This methodology was successfully applied to several 5-substituted furfurals with different amines via formation of a trienamine through...
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An approach to design reversible non-covalent inhibitors for human Granzyme B (hGrB)

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01874E, PaperMi-Sun Kim, Lauriane A. Buisson, Dean A. Heathcote, C Braddock, Anthony Barrett, Philip G Ashton-Rickardt, JP Snyder, Haipeng Hu
A structure-based design campaign for non-covalent small molecule inhibitors of human granzyme B was carried out by means of a virtual screening strategy employing three constraints and probe site-mapping with...
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Regioselective ruthenium catalysed H-D exchange using D2O as the deuterium source

Org. and Biomol. Chem. - 30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01798F, PaperLorenzo Piola, Jose A. Fernandez-Salas, Simone Manzini, Steven P. Nolan
An efficient and convenient ruthenium catalysed method for a regiospecific H/D exchange using D2O is described.
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Catalyst-Free Reductive Amination of Aromatic Aldehydes with Ammonium Formate and Hantzsch Ester

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01590H, CommunicationPan-Pan Zhao, Xin-Feng Zhou, Jian-Jun Dai, Hua-Jian Xu
The protocol of the reductive amination of aromatic aldehydes using ammonium formate and Hantzsch Ester is described. It's a mild, convenient, acid- and catalyst-free system applied for the synthesis of...
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Chemical and biological evaluation of unusual sugars, [small alpha]-aculosides, as novel Michael acceptors

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01877J, CommunicationHiromasa Ikeda, Erika Kaneko, Shunsuke Okuzawa, Daisuke Takahashi, Kazunobu Toshima
The unusual sugars [small alpha]-aculosides, which appear in certain antibiotics and have an [small alpha],[small beta]-unsaturated ketone structure, were found to be novel and selective Michael acceptors for the thiol function of cysteine...
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A straightforward modification in the thrombin binding aptamer improving stability, affinity to thrombin and nuclease resistance

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01475H, CommunicationAldo Galeone, Veronica Esposito, maria scuotto, Antonella Capuozzo, Rita Santamaria, Michela Varra, Luciano Mayol, Antonella Virgilio
Degradation of nucleic acids in biological environments is a major drawback of the therapeutic use of aptamers. Among approaches used to circumvent this negative aspect, the introduction of 3'-3' inversion...
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TBHP-promoted sequential carboxamidation and aromatisation of aryl isonitriles with formamides

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01850H, PaperJin-Tao Yu, Xiaomei Feng, Hui Zhu, Lei Wang, Yan Jiang, Jiang Cheng
The tert-butyl hydroperoxide (TBHP)-promoted sequential carboxamidation and aromatisation of isonitriles with formamides was developed. This procedure tolerates a series of functional groups, such as methyl, fluoro, chloro, acetyl, methoxy carbonyl...
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Organocatalytic enantioselective [small alpha]-amination of 5-substituted rhodanines: an efficient approach to chiral N,S-acetals

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01921K, CommunicationBaomin Wang, Huanrui Zhang, Longchen Cui, Ying Li, Jingping Qu, Yuming Song
We report a highly efficient approach to construct chiral N,S-acetals using 5-substituted rhodanines as sulfur-bound pronucleophiles catalyzed by natural cinchona alkaloids quinine or quinidine. This [small alpha]-amination reaction has a broad...
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The design, synthesis and biological evaluation of novel thiamin diphosphate analog inhibitors against pyruvate dehydrogenase multienzyme complex E1 from Escherichia coli

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01347F, Paperlingling feng, Junbo He, Haifeng He, Lulu Zhao, Lingfu Deng, Li Zhang, Lin Zhang, yanliang ren, Jian Wan, Hongwu He
Pyruvate dehydrogenase multienzyme complex E1 (PDHc E1) is a potential target enzyme for finding inhibitors to combat microbial disease. In this study, we designed and synthesized a series of novel...
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Solvent switchable cycloaddition: a (one-pot) metal-free approach towards N-substituted benzo[e]- or [f]isoindolones via Csp2-H functionalization

Org. and Biomol. Chem. - 30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01644K, PaperPratik A. Ambasana, Dipak D. Vachhani, Marzia Galli, Jeroen Jacobs, Luc Van Meervelt, Anamik K. Shah, Erik V. Van der Eycken
Solvent steers the selectivity: Green and practical Csp2-H functionalization towards N-substituted benzo[e]- or [f]isoindolones.
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Organocatalysts of oxidative protein folding inspired by protein disulphide isomerase

Org. and Biomol. Chem. - 30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01738B, CommunicationJohn C. Lukesh, Kristen A. Andersen, Kelly K. Wallin, Ronald T. Raines
Organocatalysts derived from diethylenetriamine effect the rapid isomerization of non-native protein disulfide bonds to native ones. These catalysts contain a pendant hydrophobic moiety to encourage interaction with the non-native state,...
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Relative stability of benziporphyrin and naphthiporphyrin tautomers and the emergence of macrocyclic diatropicity

Org. and Biomol. Chem. - 30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01659A, PaperDeyaa I. AbuSalim, Timothy D. Lash
The conformations and relative stabilities of a series of benziporphyrin and naphthiporphyrin tautomers were calculated and the diatropic properties of each of these species were assessed. The results were in good agreement with experimental observations and allow favorable delocalization pathways to be identified.
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Selective chromo-fluorogenic detection of DFP (a Sarin and Soman mimic) and DCNP (a Tabun mimic) with a unique probe based on a boron dipyrromethene (BODIPY) dye

Org. and Biomol. Chem. - 30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01299B, PaperAndrea Barba-Bon, Ana M. Costero, Salvador Gil, Ramon Martinez-Manez, Felix Sancenon
A new naked eye colorimetric BODIPY probe able to discriminate DCNP and DFP nerve agent mimics with good LODs.
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Synthesis of substituted quinolines via allylic amination and intramolecular Heck-coupling

Org. and Biomol. Chem. - 30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01614A, PaperSiva Murru, Brandon McGough, Radhey S. Srivastava
New catalytic approach to access substituted quinolines and naphthyridines via allylic C-H amination followed by intramolecular Heck-coupling and aerobic dehydrogenation.
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