Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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NIS-mediated oxidative cyclization of N-(2-trifluoromethyl-3-alkynyl) hydroxylamines: a facile access to 4-trifluoromethyl-5-acylisoxazoles

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01790K, PaperLi Zhang, Qin Zeng, Ao Mao, Ziang Wu, Tian Luo, Yuanjing Xiao, Junliang Zhang
A NIS mediated sequential procedure involving oxidation and electrophilic cycloisomerization of N-(2-trifluoromethyl-3-alkynyl) hydroxylamines for 4-trifluoromethyl-5-acylisoxazole synthesis is developed.
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A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from [small alpha]-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01300J, PaperXiaobing Yang, Fangzhong Hu, Hongjing Di, Xinxin Cheng, Dan Li, Xiaoli Kan, Xiaomao Zou, Qichun Zhang
A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans 2 has been developed through the domino coupling/annulations from [small alpha]-oxo ketene dithioacetals 1 and propargyl alcohols.
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Stereocontrolled lithiation/trapping of chiral 2-alkylideneaziridines: investigation into the role of the aziridine nitrogen stereodynamics

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8505-8511
DOI: 10.1039/C4OB01457J, PaperRosmara Mansueto, Leonardo Degennaro, Jean-Francois Briere, Karen Griffin, Michael Shipman, Saverio Florio, Renzo Luisi
The origin of the stereoselectivity in the lithiation/trapping of 2-alkylideneaziridines bearing a chiral group as the nitrogen substituent was investigated.
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New ganglio-tripod amphiphiles (TPAs) for membrane protein solubilization and stabilization: implications for detergent structure-property relationships

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8480-8487
DOI: 10.1039/C4OB01375A, PaperPil Seok Chae, Hyoung Eun Bae, Muhammad Ehsan, Hazrat Hussain, Jin Woong Kim
This study introduces new ganglio-TPAs with enhanced efficacy for membrane protein solubilization and stabilization compared to conventional detergents.
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Cycloreversion of [small beta]-lactams via photoinduced electron transfer

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8428-8432
DOI: 10.1039/C4OB01416B, PaperRaul Perez-Ruiz, Jose A. Saez, M. Consuelo Jimenez, Miguel A. Miranda
With DABCO as an electron donor, photoinduced cycloreversion of [small beta]-lactams leads to olefins through 1,4-radical anions and 1,4-biradicals as intermediates.
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Mechanisms for enzymatic cleavage of the N-glycosidic bond in DNA

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8367-8378
DOI: 10.1039/C4OB01063A, Review ArticleAlexander C. Drohat, Atanu Maiti
We review advances in understanding the mechanism of DNA glycosylases, emphasizing the role of the nucleobase leaving-group.
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Synthesis of L-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8415-8421
DOI: 10.1039/C4OB01319K, PaperSiddamal Reddy Putapatri, Abhinav Kanwal, Balasubramanian Sridhar, Sanjay K. Banerjee, Srinivas Kantevari
Fused chiral bicyclic 1,2,3-triazoles synthesized from commercially available natural L-rhamnose exhibited excellent SGLT inhibition activity.
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The first stereoselective total synthesis of neosemburin and isoneosemburin

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8408-8414
DOI: 10.1039/C4OB01239A, PaperGadi Madhusudhan Reddy, Perali Ramu Sridhar
The stereoselective total synthesis of neosemburin and isoneosemburin was achieved using 3-C-branched sugar precursors which in turn were synthesized by Claisen rearrangement of sugar derived allyl vinyl ethers.
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Triflic acid-promoted cycloisomerization of 2-alkynylphenyl isothiocyanates and isocyanates: a novel synthetic method for a variety of indole derivatives

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8398-8407
DOI: 10.1039/C4OB00825A, PaperTakao Saito, Yoshihiko Sonoki, Takashi Otani, Noriki Kutsumura
A unique method for synthesis of structurally diverse types of indoles involving a triflic acid-promoted cycloisomerization and a Wagner-Meerwein-type rearrangement is described.
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Copper Catalyzed Oxidative ortho-C-H Benzoxylation of 2-Phenylpyridines with Benzyl Alcohols and Benzyl Amines as Benzoxylation Sources

12 October, 2014 - 07:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01912A, PaperAshok Baburao Khemnar, Bhalchandra Mahadeo Bhanage
A simple and efficient protocol for the oxidative ortho benzoxylation of 2-phenylpyridines with benzyl alcohols and benzyl amines via C-H bond activation has been developed. Present protocol uses benzyl alcohol...
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Design and synthesis of a new dimeric xanthone derivative: enhancement of G-quadruplex selectivity and telomere damage

12 October, 2014 - 07:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01658K, PaperMarco Franceschin, Daniele Nocioni, Annamaria Biroccio, Chiara Cingolani, Emanuela Micheli, Stefano Cacchione, Alessandro Venditti, Pasquale Zizza, Armandodoriano Bianco, alessandro altieri
Following the results we previously reported on a series of xanthene and xanthone derivatives as G-quadruplex stabilizing ligands, in order to obtain a more selective compound with respect to the...
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Synthesis of Fully Functionalized Aglycone of Lycoperdinoside A and B

12 October, 2014 - 07:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01716A, Papersubhash ghosh, Balla Chandrasekhar, Sudhakar Athe, Purushotham Reddy Pothula
The communication reported the synthesis of fully functionalized aglycone of lycoperdinoside A and B. Pd-catalyzed Stille-Migita cross coupling between E-vinyl iodide 6 and E-vinyl stannane 23 established the highly substituted...
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Structures, chemotaxonomic significance, cytotoxic and Na+,K+-ATPase inhibitory activities of new cardenolides from Asclepias curassavica

12 October, 2014 - 07:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01545B, PaperRong-Rong Zhang, Hai-Yan Tian, Ya-Fang Tan, Tse-Yu Chung, Xiao-Hui Sun, Xue Xia, Wen-Cai Ye, David A. Middleton, Natalya Fedosova, Mikael Esmann, Jason T. C. Tzen, Ren-Wang Jiang
New cardenolides with potent cytotoxic and Na+,K+-ATPase inhibitory activities were isolated from the ornamental milkweed Asclepias curassavica.
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Synthesis and characterisation of glucosamine-NSAID bioconjugates

10 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8325-8335
DOI: 10.1039/C4OB01681E, PaperRachel A. Jones, Yann Thillier, Siva S. Panda, Nicole Rivera Rosario, C. Dennis Hall, Alan R. Katritzky
Synthetic strategies to prepare non-steroidal anti-inflammatory drug-glucosamine bioconjugates.
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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 - 06:54

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 - 06:54

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 - 06:54

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 - 06:54

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 - 06:54

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 - 06:54

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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