Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Synthesis of enantiomerically enriched indolines and tetrahydroisoquinolines from (S)-amino acid-derived chiral carbocations: an easy access to (3S,4R)-demethoxy-3-isopropyl diclofensine

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8318-8324
DOI: 10.1039/C4OB00922C, PaperSudipta Kumar Manna, Gautam Panda
Enantiomerically enriched indolines and tetrahydroisoquinolines were synthesized in high yields from easily accessible (S)-amino acid-derived chiral carbocations.
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Peptidomimetic inhibitors of N-myristoyltransferase from human malaria and leishmaniasis parasites

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8132-8137
DOI: 10.1039/C4OB01669F, CommunicationTayo O. Olaleye, James A. Brannigan, Shirley M. Roberts, Robin J. Leatherbarrow, Anthony J. Wilkinson, Edward W. Tate
Peptidomimetic inhibitors of N-myristoyltransferase from malaria and leishmaniasis parasites have been designed with nanomolar potency, and reveal the first direct structural evidence for a ternary NMT/CoA/myristoyl peptide product complex.
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Performance of DFT methods and origin of stereoselectivity in bipyridine N,N[prime or minute]-dioxide catalyzed allylation and propargylation reactions

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8346-8353
DOI: 10.1039/C4OB01719F, PaperDiana Sepulveda, Tongxiang Lu, Steven E. Wheeler
It is shown that many DFT methods correctly predict the stereoselectivity of bipyridine N,N[prime or minute]-dioxide catalyzed alkylation reactions despite predicting the incorrect low-lying transition state structures. A novel explanation of the origin of stereoselectivity in these reactions is also provided.
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Base-promoted annulation of [small alpha]-hydroxy ketones and dimethyl but-2-ynedioate: straightforward access to pyrano[4,3-a]quinolizine-1,4,6(2H)-triones and 2H-pyran-2,5(6H)-diones

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8128-8131
DOI: 10.1039/C4OB01858C, CommunicationHaitao He, Chaorong Qi, Yanglu Ou, Wenfang Xiong, Xiaohan Hu, Yanwei Ren, Huanfeng Jiang
A novel direct synthesis of pyrano[4,3-a]quinolizine-1,4,6(2H)-triones and 2H-pyran-2,5(6H)-diones from [small alpha]-hydroxy ketones and dimethyl but-2-ynedioate via a base-promoted cascade annulation has been developed.
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Synthesis of substituted azafluorenones from dihalogeno diaryl ketones by palladium-catalyzed auto-tandem processes

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8138-8141
DOI: 10.1039/C4OB01629G, CommunicationNada Marquise, Vincent Dorcet, Floris Chevallier, Florence Mongin
Auto-tandem processes combining either Suzuki or Heck coupling with direct cyclizing arylation are described.
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Oxidative damage of aromatic dipeptides by the environmental oxidants NO2[radical dot] and O3

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8280-8287
DOI: 10.1039/C4OB01577K, PaperL. F. Gamon, J. M. White, U. Wille
Irreversible oxidative damage at both aromatic side chains and dipeptide linkage occurs in aromatic N- and C-protected dipeptides upon exposure to the environmental pollutants NO2[radical dot] and O3.
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Enantioselective total syntheses of the proposed structures of prevezol B and evaluation of anti-cancer activity

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8239-8246
DOI: 10.1039/C4OB01662A, PaperAnna E. Leung, Riccardo Rubbiani, Gilles Gasser, Kellie L. Tuck
The first enantioselective total syntheses of the proposed structures of the natural product prevezol B are reported. This work has shown that the proposed structures of prevezol B are incorrect.
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Investigation of desilylation in the recognition mechanism to fluoride by a 1,8-naphthalimide derivative

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8275-8279
DOI: 10.1039/C4OB01500B, PaperJeeun Woo, Gunwoo Kim, Kevanie Quintero, Michael P. Hanrahan, Hector Palencia, Haishi Cao
Desilylation based fluorescence sensor (AF-1) gives a dual signal for quantitative detection of F- in MeCN.
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Annulated and bridged tetrahydrofurans from alkenoxyl radical cyclization

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8288-8307
DOI: 10.1039/C4OB01266F, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Christine Schur, Harald Kelm, Thomas Gottwald, Arne Ludwig, Rainer Kneuer, Jens Hartung
4-Pentenoxyl radicals sharing two or more carbon atoms with a cycloalkane cyclize in a predictable manner stereoselectively and regioselectively to afford in solutions of bromotrichloromethane cycloalkyl-fused or -bridged 2-bromomethyltetrahydrofurans in up to 95% yield.
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Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8204-8211
DOI: 10.1039/C4OB00978A, PaperJiuxi Chen, Leping Ye, Weike Su
Synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines and 7-benzoylindoles.
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Asymmetric total synthesis of paecilomycin E, 10[prime or minute]-epi-paecilomycin E and 6[prime or minute]-epi-cochliomycin C

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8257-8274
DOI: 10.1039/C4OB01400F, PaperPratik Pal, Nandan Jana, Samik Nanda
The asymmetric total syntheses of paecilomycin E and its stereoisomers have been disclosed by employing the late stage Mitsunobu macrolactonization reaction.
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Synthesis and SARs of indole-based [small alpha]-amino acids as potent HIV-1 non-nucleoside reverse transcriptase inhibitors

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8308-8317
DOI: 10.1039/C4OB01333F, PaperXin Han, Haoming Wu, Wei Wang, Chune Dong, Po Tien, Shuwen Wu, Hai-Bing Zhou
Indole-based [small alpha]-amino acids as potent non-nucleoside reverse transcriptase inhibitors (NNRTIs) of HIV-1 have been developed using a TZM-bl cell assay on HIV virus type HIV-1IIIB. A comprehensive SAR study of these indole [small alpha]-amino acids was also presented.
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Subtle Mitsunobu couplings under super-heating: the role of high-throughput continuous flow and microwave strategies

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8112-8124
DOI: 10.1039/C4OB01432D, Review ArticleAtul Manvar, Anamik Shah
Fragile Mitsunobu reaction can efficiently be performed under super-heating.
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Regiodivergent and short total synthesis of calothrixins

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8196-8203
DOI: 10.1039/C4OB01309C, PaperDipakranjan Mal, Joyeeta Roy, Kumar Biradha
The anionic annulation of MOM-protected furoindolone with 4-bromoquinoline followed by deprotection of the N-MOM group provides calothrixin B, whereas that with 3-bromoquinoline yields isocalothrixin B. The outcomes are explained by the divergence of the reaction mechanism from the commonly perceived 3,4-didehydroquinoline. A sequence of addition-cyclization-elimination is proposed to account for the formation of calothrixin from 4-bromoquinoline.
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Development of chemosensor for Sr2+ using organic nanoparticles: application of sensor in product analysis for oral care

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8230-8238
DOI: 10.1039/C4OB01234H, PaperSimanpreet Kaur, Amanpreet Kaur, Navneet Kaur, Narinder Singh
Organic nanoparticles have been developed and used to investigate the level of Sr2+ in an oral gel and toothpastes.
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Synthesis and spectroscopic properties of novel meso-cyano boron-pyridyl-isoindoline dyes

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8223-8229
DOI: 10.1039/C4OB01077A, PaperHui Liu, Hua Lu, Fan Wu, Zhifang Li, Nagao Kobayashi, Zhen Shen
The synthesis of meso-cyano boron-pyridyl-isoindoline dyes, a novel type of BODIPY analogue, involving a facile two-step reaction, is reported.
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Stereoselective intermolecular [2 + 2]-photocycloaddition reactions of maleic anhydride: stereocontrolled and regiocontrolled access to 1,2,3-trifunctionalized cyclobutanes

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8212-8222
DOI: 10.1039/C4OB01383B, PaperFlorian Hernvann, Gloria Rasore, Valerie Declerck, David J. Aitken
1,2,3-Trisubstituted cyclobutanes with three differentiated substituents and complementary stereochemical patterns were obtained by [2 + 2]-photocycloaddition reactions of maleic anhydride with allyl alcohol or propargyl alcohol.
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9-Amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8336-8345
DOI: 10.1039/C4OB01648C, PaperWenwen Peng, Jingwei Wan, Bing Xie, Xuebing Ma
9-Amino-(9-deoxy)cinchona alkaloid-derived chiral phase-transfer catalysts achieved high yields (92-99%) and excellent enantioselectivities (87-96% ee) in the enantioselective [small alpha]-alkylation of glycine Schiff base.
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A small synthetic molecule forms selective potassium channels to regulate cell membrane potential and blood vessel tone

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8174-8179
DOI: 10.1039/C4OB01420K, PaperHui-Yan Zha, Bing Shen, Kwok-Hei Yau, Shing-To Li, Xiao-Qiang Yao, Dan Yang
A molecule forms a K+-selective channel in the cell membrane to regulate vascular muscle cell membrane potential and blood vessel tone.
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Adaptable synthesis of C-lactosyl glycoclusters and their binding properties with galectin-3

8 October, 2014 - 05:17

Org. Biomol. Chem., 2014, 12,8180-8195
DOI: 10.1039/C4OB01374C, PaperWang Yao, Meng-jie Xia, Xiang-bao Meng, Qing Li, Zhong-jun Li
The synthesis of mono- to tetravalent C-[small beta]-lactosyl glycoclusters has been achieved in good yield. The KD values of glycoclusters against galectin-3 were tested by SPR assay, and the structure-activity relationship has been summarized in detail.
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