Royal Society of Chemistry

Synthesis of L-Rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01319K, PaperSiddamal Reddy Putapatri, Abhinav Kanwal, Sridhar Balasubramanian, Sanjay K Banerjee, Srinivas Kantevari
Herein we described synthesis of a series of novel fused bicyclic 1,2,3-triazoles from commercially available, natural deoxy sugar, L-rhamnose. The key reactions involved are i) Zn(OTf)2 catalyzed enantioselective alkynylation of...
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Friedel-Crafts Alkylations of Electron-rich Aromatics with 3-Hydroxy-2-oxindoles: Scopes and Limitations

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01264J, PaperLakshmana K. Kinthada, Santanu Ghosh, K Naresh Babu, Sharique Mohammed, Soumava Biswas, Alakesh Bisai
A Lewis acid-catalyzed nucleophilic addition of electron rich aromatics with 3-hydroxy-2-oxindoles 5 has been developed. The reaction is believed to proceed through 2H-indol-2-one ring system 9, which eventually reacts with...
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Next generation maleimides enable the controlled assembly of antibody-drug conjugates via native disulfide bond bridging

Org. and Biomol. Chem. - 18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01550A, PaperFelix F. Schumacher, Joao P. M. Nunes, Antoine Maruani, Vijay Chudasama, Mark E. B. Smith, Kerry A. Chester, James R. Baker, Stephen Caddick
Highly homogeneous ADCs are generated by the efficient bridging of interchain disulfide bonds in trastuzumab, using next generation maleimides.
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Organophosphorus-catalyzed diaza-Wittig reaction: application to the synthesis of pyridazines

Org. and Biomol. Chem. - 18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01201A, PaperHassen Bel Abed, Oscar Mammoliti, Omprakash Bande, Guy Van Lommen, Piet Herdewijn
The elaboration of the first organophosphorus-catalyzed diaza-Wittig reaction is reported.
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An Economic and Environmentally Friendly Oxidative Biaryl Coupling Promoted by Activated MnO2

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01409J, PaperJingjing Yang, Shutao Sun, Ziyu Zeng, Hongbo Zheng, Wei Li, Hongxiang Lou, Lei Liu
An activated manganese dioxide (MnO2)-BF3[round bullet, filled]OEt2 oxidation system has been developed to efficiently mediate the intramolecular as well as intermolecular biaryl coupling. The oxidative coupling proceeds smoothly at ambient temperature to...
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Ultrasonic-assisted 1,3-dipolar cycloaddition and cyclopropanation reactions for the synthesis of bis-indolizine and bis-cyclopropane derivatives

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01305K, PaperMehdi Abaszadeh, Mohammad Seifi
Ultrasound irradiation can be proceeded with 1,3-dipolar cycloaddition reaction of 2-chloropyridinium ylides with 2-benzylidenemalononitrile and 2,2'-(1,4-phenylenebis(methanylylidene))dimalononitrile to afford the indolizine and bis-indolizine derivatives respectively. While the reaction of pyridinium ylides...
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Discovery and SAR study of piperidine-based derivatives as novel influenza virus inhibitors

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01079E, PaperGuoxin Wang, Longjian Chen, Tongmei Xian, Yujie Liang, Xintao Zhang, Zhen Yang, Ming Luo
A series of piperidine-based derivatives were identified as novel and potent inhibitors of influenza virus through structural modification of the original compound that was selected from a high-throughput screen. Various...
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Diastereoselective Synthesis of Functionalized Pyrrolidines through N-Bromosuccinimide-Induced Aziridine Ring Expansion Cascade of Cinnamylaziridine

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01384K, CommunicationJing Zhou, Ying-Yeung Yeung
An efficient aziridine ring expansion cascade of cinnamylaziridine has been developed. N-Bromosuccinimide was used as the promoter. The resulting functionalized pyrrolidines are the fundamental units of many useful molecules.
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A concise synthesis of (alkynyl)(trifluoromethyl)sulfanes via a bismuth(III)-promoted reaction of trimethyl(alkynyl)silane with trifluoromethanesulfanylamide

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01451K, PaperJie Sheng, Jie Wu
A bismuth(III)-promoted reaction of trimethyl(alkynyl)silanes with trifluoromethanesulfanylamide is developed, giving rise to (alkynyl)(trifluoromethyl)sulfanes in good yields.
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Palladium-Catalyzed One Pot 2-Arylquinazoline Formation via Hydrogen-Transfer Strategy

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01296H, PaperGuo-Jun Deng, Huamin Wang, Hui Chen, Ya Chen
The palladium catalytic system was first applied to 2-arylquinazoline synthesis via hydrogen transfer methodology. Various (E)-2-nitrobenzaldehyde O-methyl oximes smoothly reacted with alcohols or benzyl amines to provide N-heterocyclic compounds in...
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A New Approach to Asymmetric Synthesis of Infectocaryone

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01162G, PaperXiubing Liu, Lingling Hu, Xiaojing Liu, Junhao Jia, Lizhen Jiang, Jiangfeng Lin, Xiaochuan Chen
A useful and flexible strategy for synthesis of (-)- and (+)-infectocaryone from commercial sugars is developed. Key step of the synthesis is an new-type Diels-Alder reaction with good chemselectivity and...
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Investigation of transannular cycloaddition reactions involving furanoxonium ions using DFT calculations. Implications for the origin of plumarellide and rameswaralide and related polycyclic metabolites isolated from corals

Org. and Biomol. Chem. - 18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00734D, PaperB. Lygo, M. J. Palframan, G. Pattenden
DFT calculations probing potential cycloaddition pathways leading to the polycyclic ring systems found in the coral secondary metabolites plumarellide, mandapamate and rameswaralide are described.
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Novel ruthenium-catalyst for hydroesterification of olefins with formates

Org. and Biomol. Chem. - 18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01246A, CommunicationIrina Profir, Matthias Beller, Ivana Fleischer
A new catalyst based on a bidentate P,N-ligand and ruthenium dodecacarbonyl for the hydroesterification of olefins with formates is reported.
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A facile manganese dioxide mediated oxidation of primary benzylamines to benzamides

Org. and Biomol. Chem. - 18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01166J, PaperA. Poeschl, D. M. Mountford
An efficient and high yielding manganese dioxide mediated oxidation of benzylamines to the corresponding amides under mild reaction conditions.
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Total synthesis of macrodiolide ionophores aplasmomycin A and boromycin via double ring contraction

Org. and Biomol. Chem. - 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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A convenient tandem one-pot synthesis of donor-acceptor-type triphenylene 2,3-dicarboxylic esters from diarylacetylene

Org. and Biomol. Chem. - 18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01503G, CommunicationChun Feng, Xian-Li Tian, Jing Zhou, Shi-Kai Xiang, Wen-Hao Yu, Bi-Qin Wang, Ping Hu, Carl Redshaw, Ke-Qing Zhao
An efficient one-pot synthetic procedure was developed for the direct preparation of polysubstituted triphenylene 2,3-dicarboxylic esters via a tandem addition process from diarylacetylene.
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Tandem Prins/pinacol reaction for the synthesis of oxaspiro[4.5]decan-1-one scaffolds

Org. and Biomol. Chem. - 18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01188K, PaperB. V. Subba Reddy, S. Gopal Reddy, M. Ramana Reddy, Manika Pal Bhadra, A. V. S. Sarma
A novel Lewis acid catalyzed Prins/pinacol cascade process has been developed for the synthesis of 7-substituted-8-oxaspiro[4.5]decan-1-ones in good yields with excellent selectivity. This is the first example of the synthesis of oxaspirocycles from aldehydes and 1-(4-hydroxybut-1-en-2-yl)cyclobutanol through a Prins/pinacol cascade.
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The effect of LNA nucleobases as enhancers for the binding of amiloride to an abasic site in DNA/DNA and DNA/RNA duplexes

Org. and Biomol. Chem. - 18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00977K, PaperYusuke Sato, Tetsushi Sato, Takaya Sato, Seiichi Nishizawa, Norio Teramae
We report on a significant effect of locked nucleic acid (LNA) nucleobases on the binding of amiloride for abasic site (AP)-containing DNA duplexes.
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An easy access to [small alpha]-aryl substituted [gamma]-ketophosphonates: Lewis acid mediated reactions of 1,3-diketones with [small alpha]-hydroxyphosphonates and tandem regioselective C-C bond cleavage

Org. and Biomol. Chem. - 18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01091D, PaperGangaram Pallikonda, Manab Chakravarty, Manoj K. Sahoo
The [small alpha]-aryl substituted (+/-)-[gamma]-ketophosphonates are produced by Lewis acid mediated reactions of [small alpha]-hydroxyphosphonates with 1,3-diketones.
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Design and synthesis of a macrosphelide A-biotin chimera

Org. and Biomol. Chem. - 18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01028K, PaperHwayoung Yun, Jaehoon Sim, Hongchan An, Jeeyeon Lee, Hun Seok Lee, Young Kee Shin, Seung-Mann Paek, Young-Ger Suh
The rational design and synthesis of a biochemical probe of natural (+)-macrosphelide A, a potent cell-cell adhesion inhibitor, was completed to aid in the identification of its biological target.
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