Royal Society of Chemistry

Trapping the Lewis acid generated transient species from pentafulvene derived diazanorbornenes with ortho-functionalized aryl iodides and aliphatic alcohols

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,3045-3061
DOI: 10.1039/C4OB00031E, PaperS. Sarath Chand, S. Saranya, P. Preethanuj, B. P. Dhanya, E. Jijy, Praveen Prakash, B. S. Sasidhar, Jan Szymoniak, P. V. Santhini, K. V. Radhakrishnan
Lewis acid catalyzed ring-opening of pentafulvene derived diazabicyclic olefins with various ortho-functionalized aryl iodides is described.
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KOAc-promoted alkynylation of [small alpha]-C-H bonds of ethers with alkynyl bromides under transition-metal-free conditions

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2969-2978
DOI: 10.1039/C4OB00002A, PaperJiajun Zhang, Pinhua Li, Lei Wang
KOAc-promoted [small alpha]-position C-H activation and alkynylation of ethers with alkynyl bromides to 2-alkynyl ethers was developed under transition-metal-free conditions.
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A fluorescent probe for estimation of adenosine diphosphate and monitoring of glucose metabolism

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,3071-3079
DOI: 10.1039/C3OB42505C, PaperArun Kumar, Parteek Prasher, Palwinder Singh
An ADP selective fluorescent probe working in aqueous medium was identified and the change in fluorescence as a function of ADP concentration was standardized.
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Tailoring fluorescent strigolactones for in vivo investigations: a computational and experimental study

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2960-2968
DOI: 10.1039/C3OB42592D, PaperCristina Prandi, Giovanni Ghigo, Ernesto G. Occhiato, Dina Scarpi, Stefano Begliomini, Beatrice Lace, Gabriele Alberto, Emma Artuso, Marco Blangetti
Fluorescent strigolactones have been designed and synthesized to fit bioimaging requirements.
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A unified strategy for the synthesis of the C1-C14 fragment of marinolic acids, mupirocins, pseudomonic acids and thiomarinols: total synthesis of pseudomonic acid methyl monate C

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2950-2959
DOI: 10.1039/C4OB00025K, PaperY. Sridhar, P. Srihari
A flexible stereoselective approach to the common C1-C14 skeleton present in natural products of the pseudomonic acid family is described.
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Amplification by nucleic acid-templated reactions

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2821-2833
DOI: 10.1039/C4OB00096J, Review ArticleJulia Michaelis, Alexander Roloff, Oliver Seitz
Nucleic acid-templated reactions that proceed with turnover provide a means for signal amplification, which facilitates the use and detection of biologically occurring DNA/RNA molecules.
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Discovery of 2[prime or minute]-hydroxychalcones as autophagy inducer in A549 lung cancer cells

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,3062-3070
DOI: 10.1039/C3OB42429D, PaperFang-Wu Wang, Sheng-Qing Wang, Bao-Xiang Zhao, Jun-Ying Miao
A series of 2[prime or minute]-hydroxychalcone derivatives was synthesized and the effects of all the compounds on growth of A549 lung cancer cell were investigated.
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Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2895-2902
DOI: 10.1039/C3OB42470G, PaperTingting Fu, Hongwei Qiao, Zhimin Peng, Gaobo Hu, Xueji Wu, Yuxing Gao, Yufen Zhao
Various valuable aryl phosphine oxides were effectively prepared via the palladium-catalyzed coupling of arylboronic acids with H-phosphine oxides.
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Triptycene-derived macrotricyclic polyether containing an anthracene unit as a powerful host for 1,2-bis(pyridium)ethane, diquat and 2,7-diazapyrenium salt

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2850-2853
DOI: 10.1039/C4OB00310A, CommunicationYa-Kun Gu, Fei Zeng, Zheng Meng, Chuan-Feng Chen
Triptycene-derived macrotricyclic polyether containing an anthracene unit was shown to be a powerful host for 1,2-bis(pyridium)ethane, diquat and 2,7-diazapyrenium salt.
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Enantioselective imine reduction catalyzed by imine reductases and artificial metalloenzymes

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2989-2992
DOI: 10.1039/C3OB42205D, Review ArticleDaniela Gamenara, Pablo Dominguez de Maria
Adding value to organic synthesis. Novel imine reductases enable the enantioselective reduction of imines to afford chiral amines. Likewise, novel bioinspired artificial metalloenzymes can perform the same reaction as well. Remarkable recent examples are herein discussed.
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The versatile enzyme Araf51 allowed efficient synthesis of rare pathogen-related [small beta]-D-galactofuranosyl-pyranoside disaccharides

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,3080-3089
DOI: 10.1039/C3OB42519C, PaperIlona Chlubnova, Blanka Kralova, Hana Dvorakova, Petr Hosek, Vojtech Spiwok, Dominik Filipp, Caroline Nugier-Chauvin, Richard Daniellou, Vincent Ferrieres
A chemo-enzymatic approach was developed for the synthesis of galactofuranosyl-containing disaccharides. The biocatalyst Araf51 was efficient in producing various rare pathogen-related [small beta]-D-galactofuranosyl-pyranosides.
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A new pyrene based highly sensitive fluorescence probe for copper(II) and fluoride with living cell application

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,3037-3044
DOI: 10.1039/C4OB00067F, PaperShyamaprosad Goswami, Shampa Chakraborty, Sima Paul, Sandipan Halder, Sukanya Panja, Subhra Kanti Mukhopadhyay
A new pyrene based fluorescence probe has been synthesized for fluorogenic detection of Cu2+ in acetonitrile-aqueous media (7:3 CH3CN-HEPES buffer v/v, pH 7.5) with the bioimaging in both prokaryotic and eukaryotic living cells.
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A Pd-based regioselective strategy to indole-1,2-fused 8- and 9-membered rings: their evaluation as potential scaffolds for apoptosis in zebrafish

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2864-2868
DOI: 10.1039/C4OB00140K, CommunicationBagineni Prasad, B. Yogi Sreenivas, Araka Sushma, Swapna Yellanki, Raghavender Medisetti, Pushkar Kulkarni, Manojit Pal
A Pd-based strategy afforded novel indoles as potential scaffolds for apoptosis.
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Cation[small pi] interaction and microhydration effects in complexes formed by pyrrolidinium cation and aromatic species in amino acid side chains

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2938-2949
DOI: 10.1039/C3OB42388C, PaperAna A. Rodriguez-Sanz, Enrique M. Cabaleiro-Lago, Jesus Rodriguez-Otero
Microhydration deeply affects the characteristics of pyrrolidinium cation complexes with aromatic units found in amino acid side chains.
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Copper-mediated trifluoromethylation of propargyl acetates leading to trifluoromethyl-allenes

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2903-2906
DOI: 10.1039/C3OB42575D, PaperYun-Long Ji, Jun-Jie Kong, Jin-Hong Lin, Ji-Chang Xiao, Yu-Cheng Gu
A copper-promoted trifluoromethylation of propargyl acetates with S-(trifluoromethyl)diphenylsulfonium triflate leading to trifluoromethyl-allenes under mild conditions is described.
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Quadrupolar, emission-tunable [small pi]-expanded 1,4-dihydropyrrolo[3,2-b]pyrroles - synthesis and optical properties

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2874-2881
DOI: 10.1039/C4OB00143E, PaperAnita Janiga, Dominika Bednarska, Bjarne Thorsted, Jonathan Brewer, Daniel T. Gryko
A-D-A chromophores containing pyrrolo[3,2-b]pyrrole, as a central donor moiety, display blue, turquoise, yellow and orange fluorescence, depending on the strength of the electron-withdrawing substituent.
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A general synthetic strategy and the anti-proliferation properties on prostate cancer cell lines for natural phenylethanoid glycosides

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2926-2937
DOI: 10.1039/C3OB42503G, PaperShaheen K. Mulani, Jih-Hwa Guh, Kwok-Kong Tony Mong
The total synthesis of natural glycosides for the anti-proliferation of cancer cell lines.
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Complexity generation by chemical synthesis: a five-step synthesis of (-)-chaetominine from L-tryptophan and its biosynthetic implications

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2859-2863
DOI: 10.1039/C4OB00314D, CommunicationChu-Pei Xu, Shi-Peng Luo, Ai-E Wang, Pei-Qiang Huang
We demonstrated, for the first time, that the hexacyclic peptidyl alkaloid (-)-chaetominine (1) can be synthesized in a straightforward manner from L-Trp, which could be helpful in understanding the biosynthetic pathway of (-)-chaetominine (1).
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Gold-catalysed cyclisation of N-propargylic [small beta]-enaminones to form 3-methylene-1-pyrroline derivatives

Org. and Biomol. Chem. - 17 April, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,2869-2873
DOI: 10.1039/C3OB42513D, CommunicationKommuru Goutham, N. S. V. M. Rao Mangina, Surisetti Suresh, Pallepogu Raghavaiah, Galla V. Karunakar
A gold(I) catalysed reaction between N-propargylic [small beta]-enaminones and arynes was developed to access 3-methylene-1-pyrrolines. The title compounds were obtained in 57-78% yields.
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Palladium(II)-catalysed total synthesis of naturally occurring pyrano[3,2-a]carbazole and pyrano[2,3-b]carbazole alkaloids

Org. and Biomol. Chem. - 17 April, 2014 - 11:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00367E, PaperHans-Joachim Knolker, Ronny Hesse, Anne Jager, Arndt W. Schmidt
Seven naturally occurring pyranocarbazole alkaloids (pyrayafoline A-E, O-methylmurrayamine A and O-methylmahanine) have been obtained by total synthesis using a palladium(II)-catalysed oxidative cyclisation of a diarylamine to an orthogonally diprotected 2,7-dihydroxycarbazole...
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