Org. and Biomol. Chem.

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Formal synthesis of (+)-3-epi-eupomatilone-6 and the 3,5-bis-epimer

18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,6885-6894
DOI: 10.1039/C4OB01078G, PaperSariya Yodwaree, Darunee Soorukram, Chutima Kuhakarn, Patoomratana Tuchinda, Vichai Reutrakul, Manat Pohmakotr
The formal synthesis of (+)-3-epi-eupomatilone-6 and the 3,5-bis-epimer has been accomplished using stereoselective conjugate addition of vinylmagnesium chloride to a chiral [small alpha],[small beta]-unsaturated N-acyl oxazolidinone followed by [small alpha]-methylation as the key steps.
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Ligand-free MCR for linking quinoxaline framework with a benzimidazole nucleus: a new strategy for the identification of novel hybrid molecules as potential inducers of apoptosis

18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,6800-6805
DOI: 10.1039/C4OB01268B, CommunicationRajnikanth Sunke, P. Vijaya Babu, Swapna Yellanki, Raghavender Medishetti, Pushkar Kulkarni, Manojit Pal
A Cu-catalyzed MCR afforded novel hybrid molecules as potential inducers of apoptosis in zebrafish.
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An enzymatic approach to bifunctional chelating agents

18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,6915-6921
DOI: 10.1039/C4OB00810C, PaperPaolo Minazzi, Luciano Lattuada, Ivan G. Menegotto, Giovanni B. Giovenzana
Three novel BFCAs are obtained through an original protocol involving an enzymatic hydrolysis as the key step.
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Highly selective fluorescence off-on probes for biothiols and imaging in live cells

18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,6837-6841
DOI: 10.1039/C4OB01031K, PaperDi Zhang, Wei Chen, Jianming Kang, Yong Ye, Yufen Zhao, Ming Xian
Three sulfonyl benzothiazole-based fluorescence off-on probes for biothiols are developed and applied for visualizing endogenous thiols in living cells.
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Design, synthesis and biological evaluation of bicyclic iminosugar hybrids: conformational constraint as an effective tool for tailoring the selectivity of [small alpha]-glucosidase inhibitors

18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,6855-6868
DOI: 10.1039/C4OB00486H, PaperInderpreet Arora, Vivek Kr. Kashyap, Alok Kumar Singh, Arunava Dasgupta, Brijesh Kumar, Arun K. Shaw
Selective inhibition by conformational restriction of pyrrolidine iminosugars. Click conceived pyrrolidotriazoles incorporate essential features to access the mimicry of the transition state of carbohydrate processing enzymes.
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Scandium-catalyzed tandem selective oxirane ring-opening/Friedel-Crafts alkylation: a facile access to [1,4]oxazino[4,3-a]indoles and 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines

18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,6869-6877
DOI: 10.1039/C4OB01057D, PaperLai Wei, Lu Liu, Junliang Zhang
An efficient Lewis acid-catalyzed tandem selective ring-opening and Friedel-Crafts alkylation of 1H-indol-1-yl derived oxiranes was developed.
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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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