Org. and Biomol. Chem.

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Copper-catalysed direct radical alkenylation of alkyl bromides

18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,6790-6793
DOI: 10.1039/C4OB00813H, CommunicationXu Zhang, Hong Yi, Zhixiong Liao, Guoting Zhang, Chao Fan, Chu Qin, Jie Liu, Aiwen Lei
A copper-catalysed direct radical alkenylation of benzyl bromides and [small alpha]-carbonyl alkyl bromides has been developed. Compared with recent radical alkenylations which mostly focused on secondary or tertiary alkyl halides, this transformation shows good reactivity towards primary alkyl halides and tertiary/secondary alkyl halides are also tolerated.
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Facile synthesis of 5H-benzo[b]carbazol-6-yl ketones via sequential reaction of Cu-catalyzed Friedel-Crafts alkylation, iodine-promoted cyclization, nucleophilic substitution and aromatization

18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,6806-6811
DOI: 10.1039/C4OB00815D, CommunicationJing Wu, Dongping Wang, Haolong Wang, Fan Wu, Xincheng Li, Boshun Wan
A convenient method to access 5H-benzo[b]carbazol-6-yl ketones from indoles and 2-(2-(alkynyl)benzylidene)malonates has been developed.
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A tryptophan responsive fluorescent and wettable dual-signal switch

18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,6824-6830
DOI: 10.1039/C4OB00792A, PaperXiaoyan Zhang, Jing Li, Ningmei Feng, Li Luo, Zhen Dai, Li Yang, Demei Tian, Haibing Li
A new fluorescent dianthracene calix[4]arene (C4DA) was designed and synthesized via coupling the fluorescent anthracene units and calix[4]arene units.
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Rhodium(III)-catalyzed regioselective C2-amidation of indoles with N-(2,4,6-trichlorobenzoyloxy)amides and its synthetic application to the development of a novel potential PPAR[gamma] modulator

18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,6831-6836
DOI: 10.1039/C4OB00637B, PaperJingjing Shi, Guanguan Zhao, Xiaowei Wang, H. Eric Xu, Wei Yi
Here an efficient rhodium(III)-catalyzed C2-amidation of indoles and its synthetic application to a new PPAR[gamma] modulator have been developed.
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Total synthesis of macrodiolide ionophores aplasmomycin A and boromycin via double ring contraction

18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01017E, PaperMitchell A. Avery, Satish C. Choudhry, Om Prakash Dhingra, Brian D. Gray, Myung-chol Kang, Shen-chun Kuo, Thalathani R. Vedananda, James D. White, Alan J. Whittle
Aplasmomycin A was synthesized by double ring contraction of a 34-membered dilactone; boromycin was synthesized using the same strategy.
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Iridium(I) hydroxides in catalysis: rearrangement of allylic alcohols to ketones

16 August, 2014 - 17:17

Org. Biomol. Chem., 2014, 12,6672-6676
DOI: 10.1039/C4OB01428F, PaperDavid J. Nelson, Jose A. Fernandez-Salas, Byron J. Truscott, Steven P. Nolan
The iridium(I) hydroxide complex [Ir(OH)(COD)(IiPr)] has been shown to be a competent catalyst for the rearrangement of allylic alcohols to ketones.
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Diaporine, a novel endophyte-derived regulator of macrophage differentiation

14 August, 2014 - 16:54

Org. Biomol. Chem., 2014, 12,6545-6548
DOI: 10.1039/C4OB01123F, CommunicationHao Chen Wu, Hui Ming Ge, Le Yun Zang, Yun Cheng Bei, Zhi Yuan Niu, Wei Wei, Xiu Jing Feng, Sen Ding, Seik Weng Ng, Ping Ping Shen, Ren Xiang Tan
Diaporine (1), an unprecedented symmetric polyketide, was characterized from the endophytic fungus Diaporthe sp. Diaporine was demonstrated to inhibit significantly the differentiation of macrophages.
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Recent advances in trifluoromethylation of organic compounds using Umemoto's reagents

14 August, 2014 - 16:54

Org. Biomol. Chem., 2014, 12,6580-6589
DOI: 10.1039/C4OB00671B, Review ArticleCai Zhang
This review highlights recent developments in the direct introduction of a trifluoromethyl group into organic compounds with Umemoto's reagents.
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Folded alkyl chains in water-soluble capsules and cavitands

14 August, 2014 - 16:54

Org. Biomol. Chem., 2014, 12,6561-6563
DOI: 10.1039/C4OB01032A, CommunicationJesse V. Gavette, Kang-Da Zhang, Dariush Ajami, Julius Rebek
A deep cavitand with ionic "feet" dimerizes around hydrophobic compounds in D2O.
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A study on the chiral inversion of mandelic acid in humans

14 August, 2014 - 16:54

Org. Biomol. Chem., 2014, 12,6737-6744
DOI: 10.1039/C3OB42515K, PaperMaksims Yevglevskis, Catherine R. Bowskill, Chloe C. Y. Chan, Justin H.-J. Heng, Michael D. Threadgill, Timothy J. Woodman, Matthew D. Lloyd
Mandelic acid 1 undergoes uni-directional chiral inversion in mammalian cells by a separate pathway to that of Ibuprofen 3.
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A lysosome-targeted drug delivery system based on sorbitol backbone towards efficient cancer therapy

14 August, 2014 - 16:54

Org. Biomol. Chem., 2014, 12,6564-6569
DOI: 10.1039/C4OB01153H, CommunicationSanthi Maniganda, Vandana Sankar, Jyothi B. Nair, K. G. Raghu, Kaustabh K. Maiti
A lysosome-targeted drug delivery system utilizing sorbitol scaffold linked to octa-guanidine and to a peptide substrate of lysosomal cysteine protease, cathepsin B.
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Metal-free oxidative olefination of primary amines with benzylic C-H bonds through direct deamination and C-H bond activation

14 August, 2014 - 16:54

Org. Biomol. Chem., 2014, 12,6557-6560
DOI: 10.1039/C4OB01025F, CommunicationLiang Gong, Li-Juan Xing, Tong Xu, Xue-Ping Zhu, Wen Zhou, Ning Kang, Bin Wang
An oxidative olefination reaction between aliphatic primary amines and benzylic sp3 C-H bonds has been achieved using N-bromosuccinimide as catalyst and tert-butyl hydroperoxide as oxidant.
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Asymmetric borylation of [small alpha],[small beta]-unsaturated esters catalyzed by novel ring expanded N-heterocyclic carbenes based on chiral 3,4-dihydro-quinazolinium compounds

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6554-6556
DOI: 10.1039/C4OB01101E, CommunicationLiliang Huang, Yong Cao, Manping Zhao, Zhongfeng Tang, Zhihua Sun
A series of novel ring expanded N-heterocyclic carbene (NHC) precursors were synthesized, which showed excellent enantioselectivities for borylation of [small alpha],[small beta]-unsaturated esters.
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Demonstration of a common indole-based aromatic core in natural and synthetic eumelanins by solid-state NMR

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6730-6736
DOI: 10.1039/C4OB01066C, PaperSubhasish Chatterjee, Rafael Prados-Rosales, Sindy Tan, Boris Itin, Arturo Casadevall, Ruth E. Stark
Comparing natural and synthetic eumelanin pigment structures: high-field 2D solid-state NMR reveals a common indole-based aromatic core for ubiquitous protective pigments that inspire engineered materials.
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N-Bromoacetamide-mediated domino cyclization and elimination of homoallylic trichloroacetimidates: a novel approach toward the synthesis of 1-bromo-2-amino-3-butene derivatives

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6653-6660
DOI: 10.1039/C4OB01126K, PaperRui Zhu, Kai Yu, Zhenhua Gu
Allylic amides 3 were synthesized efficiently from homoallylic trichloroacetimidates 1via domino bromo-cyclization and elimination reactions.
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Novel phthalamides containing sulfiliminyl moieties and derivatives as potential ryanodine receptor modulators

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6643-6652
DOI: 10.1039/C4OB00716F, PaperSha Zhou, Tao Yan, Yuxin Li, Zhehui Jia, Baolei Wang, Yu Zhao, Yuanyuan Qiao, Lixia Xiong, Yongqiang Li, Zhengming Li
The present work firstly reported that the new diamides incorporating sulfiliminyl moieties are potential candidate structures for new ryanodine receptor modulators.
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Enhanced catalysis and enantioselective resolution of racemic naproxen methyl ester by lipase encapsulated within iron oxide nanoparticles coated with calix[8]arene valeric acid complexes

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6634-6642
DOI: 10.1039/C4OB01048E, PaperSerkan Sayin, Enise Akoz, Mustafa Yilmaz
In this study, two types of nanoparticles have been used as additives for the encapsulation of Candida rugosa lipase via the sol-gel method.
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An acridinium-based sensor as a fluorescent photoinduced electron transfer probe for proton detection modulated by anionic micelles

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6677-6683
DOI: 10.1039/C4OB00559G, PaperStefano Basili, Tiziana Del Giacco, Fausto Elisei, Raimondo Germani
Photoinduced electron transfer has been demonstrated to be the quenching mechanism for the fluorescent pH sensor based on the 9-amino-10-methylacridinium chromophore. The presence of anionic micelles causes a significant increase in the detection sensitivity of pH.
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SN2 regioselectivity in the esterification of 5- and 7-membered azacycloalkane quaternary salts: a DFT study to reveal the transition state ring conformation prevailing over the ground state ring strain

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6717-6724
DOI: 10.1039/C4OB00695J, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Akihiro Kimura, Susumu Kawauchi, Takuya Yamamoto, Yasuyuki Tezuka
SN2 regioselectivity in 5- and 7-membered azacycloalkanes quaternary salts is directed by the transition state ring conformation.
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Synthesis and evaluation of antineurotoxicity properties of an amyloid-[small beta] peptide targeting ligand containing a triamino acid

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6684-6693
DOI: 10.1039/C4OB00959B, PaperDmytro Honcharenko, Partha Pratim Bose, Jyotirmoy Maity, Firoz Roshan Kurudenkandy, Alok Juneja, Erik Floistrup, Henrik Biverstal, Jan Johansson, Lennart Nilsson, Andre Fisahn, Roger Stromberg
A new triamino acid enables synthesis of an amyloid-[small beta] peptide (A[small beta]) targeting ligand with additional A[small beta]-ligand interactions that gives protection towards A[small beta]-induced reduction of gamma oscillations in hippocampal slice preparation.
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