Royal Society of Chemistry

Isopropylmagnesium Chloride-promoted Unilateral Addition of Grignards to [small beta]-Diketones: One-pot Syntheses of [small beta]-Tertiary Alcohol Ketones or 3-Substituted Cyclic-2-Enones

Org. and Biomol. Chem. - 16 November, 2015 - 06:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB02072G, PaperRui Yuan, Dan Zhao, Li-Yuan Zhang, Xiang Pan, Yan Yang, Pei Wang, Hong-Feng Li, Chao-Shan Da
The regioselective unilateral additions of Grignards to acyclic or cyclic [small beta]-diketones were effectively promoted by sub-stoichiometric amount of i-PrMgCl to afford [small beta]-tertiary alcohol ketones or 3-substituted cyclic-2-enones respectively. Also addition...
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Fluorine in fragrances: Exploring the difluoromethylene (CF2) group as a conformational constraint in macrocyclic musk lactones

Org. and Biomol. Chem. - 16 November, 2015 - 06:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB02023A, PaperMichael J Corr, Rodrigo A Cormanich, Cortney N von Hahmann, Michael Buehl, David Bradford Cordes, Alexandra Slawin, David O'Hagan
The CF2 group is incorporated into specific positions within the lactone ring of the natural musk lactone, (12R)-(+)-12-methyl-13-tridecanolide, a constituent of Angelica root oil, Angelica archangelica L. The approach is...
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Synthesis and biological evaluation of analogs of AAL(S) for use as ceramide synthase 1 inhibitors

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2016, Advance Article
DOI: 10.1039/C5OB01931A, CommunicationHamish D. Toop, Anthony S. Don, Jonathan C. Morris
This work has led to the identification of a selective CerS1 inhibitor that is non-cytotoxic.
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On the association of neutral and cationic tris(tetrathiafulvaleno)dodecadehydro[18]annulenes

Org. and Biomol. Chem. - 16 November, 2015 - 06:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB02087E, CommunicationChristian Richard Parker, Kasper Lincke, Mikkel A. Christensen, Karol Luspai, P. Rapta, Thomas J Sorensen, Thorbjorn J. Morsing, Lin Du, Henrik Kjaergaard, Ole Hammerich, Francois Diederich, Mogens Brondsted Nielsen
Here, we report the first X-ray crystal structure of a tetrathiafulvalene-fused dehydroannulene with peripheral ethylthio substituents. In addition, we have subjected this compound to electrochemical and UV-Vis-NIR/ESR spectroelectrochemical studies to...
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NMR analysis of the binding mode of two fungal endo [small beta]-1,4-mannanases from GH5 and GH26 families

Org. and Biomol. Chem. - 16 November, 2015 - 06:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01851J, PaperRoberta Marchetti, Jean-Guy Berrin, Marie Couturier, Shah Ali Ul Qader, Antonio Molinaro, Alba Silipo
The enzymatic digestion of the main components of lignocellulosic biomass, including plant cell wall mannans, constitutes a fundamental step in the renewable biofuel production, with great potential benefit in the...
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Enantioselective oxidative boron Heck reactions

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2016, Advance Article
DOI: 10.1039/C5OB01984B, Review ArticleOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.A.-L. Lee
This review highlights the use of the oxidative boron Heck reaction in enantioselective Heck-type couplings.
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Iodine-catalyzed expeditious synthesis of sulfonamides from sulfonyl hydrazides and amines

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB02075A, PaperSirilata Yotphan, Ladawan Sumunnee, Danupat Beukeaw, Chonchanok Buathongjan, Vichai Reutrakul
A new synthesis of sulfonamides via an iodine-catalyzed sulfonylation of amines with arylsulfonyl hydrazides at room temperature is reported.
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One pot oxidative N-S bond formation to access 2-sulfenylimine chromenes

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01790D, PaperAshok Kale, Madhu Chennapuram, Chiranjeevi Bingi, Jagadeesh Babu Nanubolu, Krishnaiah Atmakur
Synthesis of 2-sulfenylimine chromene compounds is accomplished in a one-pot, catalyst-free, five-component reaction in toluene. When aniline was employed as nucleophile formation of hexahydrobenzofuran-2-N-phenyl carboxamide was observed. Excellent yields, simple reaction conditions high compatibility are the advantages of this protocol.
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A diphenyl ether derived bidentate secondary phosphine oxide as a preligand for nickel-catalyzed C-S cross-coupling reactions

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, 13,10802-10807
DOI: 10.1039/C5OB01874A, CommunicationNadeesha P. N. Wellala, Hairong Guan
A bidentate secondary phosphine oxide is a more effective preligand than Ph2P(O)H in nickel-catalyzed C-S cross-coupling reactions.
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Molecular binding behaviors and thermodynamics of ferrocenyl dimethylaminium derivatives by anionic pillar[5]arene

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, 13,10808-10812
DOI: 10.1039/C5OB01884F, CommunicationCui-Fang Zhang, Sheng-Hua Li, Cai-Cai Zhang, Yu Liu
A novel anionic water-soluble pillar[5]arene (4C-WP5A) was synthesized via a convenient synthetic strategy of the direct cyclization of a functionalized hydroquinone monomer.
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Conformational promiscuity in triazolamers derived from quaternary amino acids mimics peptide behaviour

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, 13,10797-10801
DOI: 10.1039/C5OB01461A, CommunicationJordi Sola, Michael Bolte, Ignacio Alfonso
Oligomers made by click chemistry display a duality of secondary structures similar to natural peptides as inferred by NMR spectroscopy and X-ray diffraction experiments.
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Late stage modification of receptors identified from dynamic combinatorial libraries

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, 13,10939-10945
DOI: 10.1039/C5OB01649E, PaperNicholas K. Pinkin, Amanie N. Power, Marcey L. Waters
Approaches for the late-stage modification of receptors discovered from dynamic combinatorial libraries and the investigation of the effects of simple modifications on receptor binding and selectivity.
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4[small pi] electrocyclisation in domino processes: contemporary trends and synthetic applications towards natural products

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, 13,10774-10796
DOI: 10.1039/C5OB01703C, Review ArticleNadeem S. Sheikh
Recent most illustrative examples dealing with 4[small pi] electrocyclisation in domino reactions, along with a precise mechanistic insight and its synthetic utility towards bioactive natural products are concisely reviewed.
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B(OCH2CF3)3-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, 13,10888-10894
DOI: 10.1039/C5OB01801C, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Valerija Karaluka, Rachel M. Lanigan, Paul M. Murray, Matthew Badland, Tom D. Sheppard
The direct amidation of pharmaceutically relevant carboxylic acids and amines with B(OCH2CF3)3 in cyclopentyl methyl ether (CPME) is described.
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Versatile synthesis of oxime-containing acyclic nucleoside phosphonates - synthetic solutions and antiviral activity

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, 13,10946-10956
DOI: 10.1039/C5OB01571E, PaperPavel N. Solyev, Maxim V. Jasko, Alla A. Kleymenova, Marina K. Kukhanova, Sergey N. Kochetkov
New oxime-containing acyclic nucleoside phosphonates 9-{2-[(phosphonomethyl)oximino]ethyl}adenine (1), -guanine (2) and 9-{2-[(phosphonomethyl)oximino]propyl}adenine (3) with wide spectrum activity against different types of viruses were synthesized.
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Chemically synthesized dicarba H2 relaxin analogues retain strong RXFP1 receptor activity but show an unexpected loss of in vitro serum stability

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, 13,10895-10903
DOI: 10.1039/C5OB01539A, PaperMohammed Akhter Hossain, Linda M. Haugaard-Kedstrom, K. Johan Rosengren, Ross A. D. Bathgate, John D. Wade
Replacement of a disulfide bond with a non-reducible dicarba bond in an insulin-like peptide, relaxin, did not significantly alter functional activity but resulted in unexpected dramatic decrease in vitro serum stability.
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Thiourea-based spacers in potent divalent inhibitors of Pseudomonas aeruginosa virulence lectin LecA

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, 13,10923-10928
DOI: 10.1039/C5OB01452B, PaperAliaksei V. Pukin, Arwin J. Brouwer, Leonie Koomen, H. C. Quarles van Ufford, Johan Kemmink, Nico J. de Mol, Roland J. Pieters
A thiourea spacer adopts an extended conformation and forms the basis of a potent bivalent ligand for Pseudomonas aeruginosa lectin LecA.
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A mild and fast continuous-flow trifluoromethylation of coumarins with the CF3 radical derived from CF3SO2Na and TBHP

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, 13,10917-10922
DOI: 10.1039/C5OB01516B, PaperXiaodan Zhang, Ping Huang, Yaming Li, Chunying Duan
A mild and fast Cu(I)-catalyzed trifluoromethylation of coumarins with CF3SO2Na and TBHP in a continuous-flow reactor has been developed.
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Chelate cooperativity effects on the formation of di- and trivalent pseudo[2]rotaxanes with diketopiperazine threads and tetralactam wheels

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, 13,10881-10887
DOI: 10.1039/C5OB01687H, PaperNora L. Traulsen, Christoph H.-H. Traulsen, Peter M. Deutinger, Sebastian Muller, Deborah Schmidt, Igor Linder, Christoph A. Schalley
Double mutant cycle analyses of isothermal titration calorimetry data on di- and trivalent amide pseudorotaxanes provide insight into chelate cooperativity effects on multiply threaded structures.
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3D shapes of aryl(dihydro)naphthothiophenes: a comprehensive and structural study

Org. and Biomol. Chem. - 16 November, 2015 - 06:54

Org. Biomol. Chem., 2015, 13,10844-10851
DOI: 10.1039/C5OB01583A, PaperH. Boufroura, A. Souibgui, A. Gaucher, J. Marrot, G. Pieters, F. Aloui, B. Ben Hassine, G. Clavier, D. Prim
The overall shapes of aryl(dihydro)naphthothiophenes depend on steric and electronic key parameters.
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