Org. and Biomol. Chem.

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A one-pot multicomponent coupling/cyclization for natural product herbicide (+/-)-thaxtomin A

4 August, 2014 - 14:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01148A, CommunicationJean Paul Bourgault, Amarendar Reddy Maddirala, Peter R. Andreana
The herbicide (+/-)-thaxtomin A has been synthesized in a one-pot two step process through an Ugi reaction followed by base-mediated cyclization.
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The first stereoselective total synthesis of neosemburin and isoneosemburin

4 August, 2014 - 14:17

Org. Biomol. Chem., 2014, Advance Article
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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Relative contractile motion of the rings in a switchable palindromic [3]rotaxane in aqueous solution driven by radical-pairing interactions

4 August, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,6089-6093
DOI: 10.1039/C4OB01228C, CommunicationLeah S. Witus, Karel J. Hartlieb, Yuping Wang, Aleksandrs Prokofjevs, Marco Frasconi, Jonathan C. Barnes, Edward J. Dale, Albert C. Fahrenbach, J. Fraser Stoddart
This communication describes a mechanically interlocked molecule (MIM), capable of switchable and reversible linear molecular motion.
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1,1,1,3,3,3-Hexafluoro-2-propanol and 2,2,2-trifluoroethanol solvents induce self-assembly with different surface morphology in an aromatic dipeptide

2 August, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,6181-6189
DOI: 10.1039/C4OB00821A, PaperSamala Murali Mohan Reddy, Ganesh Shanmugam, Asit Baran Mandal
1,1,1,3,3,3-Hexafluoro-2-propanol and 2,2,2-trifluoroethanol solvents, which are known to disaggregate self-assembled peptides, induce the self-assembly of aromatic dipeptides to give structures with different surface morphologies.
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Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach

2 August, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,6121-6127
DOI: 10.1039/C4OB01142B, PaperAdam D. J. Calow, Elena Fernandez, Andrew Whiting
Efficient, catalytic, asymmetric total syntheses of both (R)-fluoxetine and (S)-duloxetine from [small alpha],[small beta]-unsaturated aldehydes are reported.
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A fluorescent probe for intracellular cysteine overcoming the interference by glutathione

2 August, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,6128-6133
DOI: 10.1039/C4OB00382A, PaperMinggang Tian, Fuqiang Guo, Yuming Sun, Weijia Zhang, Fang Miao, Yong Liu, Guofen Song, Cheuk-Lam Ho, Xiaoqiang Yu, Jing Zhi Sun, Wai-Yeung Wong
A fluorescent probe was reported to discriminate 30-200 [small mu ]M cysteine, overcoming the interference by 1-10 mM glutathione. The selectivity was also proved by cellular experiments.
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Copper-catalyzed annulation of heteroaromatic [small beta]-halo-[small alpha],[small beta]-unsaturated carboxylic acids with alkynes for the synthesis of indolo[2,3-c]pyrane-1-ones and thieno[2,3-c]pyrane-7-ones

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6114-6120
DOI: 10.1039/C4OB00996G, PaperDa-Wei Gu, Xun-Xiang Guo
Efficient synthesis of indolo[2,3-c]pyrane-1-ones and thieno[2,3-c]pyrane-7-ones was achieved via annulation of heteroaromatic [small beta]-halo-[small alpha],[small beta]-unsaturated carboxylic acids with alkynes.
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TFAA/H3PO4 mediated unprecedented N-acylation of carbazoles leading to small molecules possessing anti-proliferative activities against cancer cells

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6080-6084
DOI: 10.1039/C4OB00686K, CommunicationSunder Kumar Kolli, Bagineni Prasad, P. Vijaya Babu, Mohd Ashraf Ashfaq, Nasreen Z. Ehtesham, R. Ramesh Raju, Manojit Pal
TFAA/H3PO4-mediated unusual N-acylation of carbazoles afforded potential anti-proliferative agents.
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Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6072-6075
DOI: 10.1039/C4OB01159G, CommunicationChunhuan He, Xuewei Qian, Peipei Sun
Thiol (selenol) esters were synthesized by a direct oxidative coupling reaction of aldehydes with disulfides (diselenides) under metal-free conditions.
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3-NO2-5,10,15-triarylcorrolato-Cu as a versatile platform for synthesis of novel 3-functionalized corrole derivatives

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6200-6207
DOI: 10.1039/C4OB01247J, PaperM. Stefanelli, M. Mancini, M. Raggio, S. Nardis, F. R. Fronczek, G. T. McCandless, K. M. Smith, R. Paolesse
By way of a [small beta]-acylated copper corrolate, a novel corrole derivative bearing an alkyl azide group on the peripheral positions was obtained and successfully exploited in click chemistry reactions.
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Deciphering aromaticity in porphyrinoids via adaptive natural density partitioning

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6145-6150
DOI: 10.1039/C4OB01018C, PaperAlexander S. Ivanov, Alexander I. Boldyrev
Aromaticity in porphyrins is described by the adaptive natural density partitioning analysis.
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The Escherichia coli glucuronylsynthase promoted synthesis of steroid glucuronides: improved practicality and broader scope

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6208-6214
DOI: 10.1039/C4OB00984C, PaperPaul Ma, Nicholas Kanizaj, Shu-Ann Chan, David L. Ollis, Malcolm D. McLeod
Steroid glucuronides can be quickly and conveniently prepared on the milligram scale using the E. coli glucuronylsynthase enzyme followed by purification with solid-phase extraction.
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Iron-catalyzed tetrasubstituted alkene formation from alkynes and sodium sulfinates

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6076-6079
DOI: 10.1039/C4OB00816B, CommunicationSaiwen Liu, Lichang Tang, Hui Chen, Feng Zhao, Guo-Jun Deng
An iron-catalyzed sulfenylation and arylation of alkynes with aryl sulfinic acid sodium salts is described.
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Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6190-6199
DOI: 10.1039/C4OB01088D, PaperDavid E. Stephens, Gabriel Chavez, Martin Valdes, Monica Dovalina, Hadi D. Arman, Oleg V. Larionov
Novel and efficient method of direct perfluoroalkylation of azine N-oxides has been developed and interesting mechanistic details have been provided.
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Balanced [small pi]-[small pi] interactions directing the self-assembly of indolocarbazole-based low molecular mass organogelators

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6134-6144
DOI: 10.1039/C4OB00873A, PaperPeng Gong, Pengchong Xue, Chong Qian, Zhenqi Zhang, Ran Lu
New indolocarbazole-based organogelators emitting strong blue light have been synthesized.
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Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6151-6166
DOI: 10.1039/C4OB00841C, PaperTran Quang Hung, Do Huy Hoang, Ngo Ngoc Thang, Tuan Thanh Dang, Khurshid Ayub, Alexander Villinger, Aleksej Friedrich, Stefan Lochbrunner, Gerd-Uwe Flechsig, Peter Langer
A series of indolo[2,3-b]quinoxaline derivatives were efficiently synthesized from 2,3-dibromoquinoxaline by two pathways.
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Reactivity in the nucleophilic aromatic substitution reactions of pyridinium ions

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6175-6180
DOI: 10.1039/C4OB00946K, PaperJeannette T. Bowler, Freeman M. Wong, Scott Gronert, James R. Keeffe, Weiming Wu
The nucleophilic aromatic substitution reactions of piperidine with N-methylpyridinium ions in methanol occur via rate determining preassociation of a second piperidine molecule with the addition intermediate followed by barrier-free deprotonation. Loss of leaving group is concurrent with deprotonation for Cl, Br, and I (E2), but subsequent to deprotonation, although rapid, for CN and F (E1cBIRR).
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Synthesis, and the antioxidant, neuroprotective and P-glycoprotein induction activity of 4-arylquinoline-2-carboxylates

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6267-6277
DOI: 10.1039/C4OB00488D, PaperJaideep B. Bharate, Abubakar Wani, Sadhana Sharma, Shahi Imam Reja, Manoj Kumar, Ram A. Vishwakarma, Ajay Kumar, Sandip B. Bharate
An efficient synthesis of 4-arylquinoline-2-carboxylates and their antioxidant, neuroprotective and P-glycoprotein induction activity have been described.
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6-Azido hyacinthacine A2 gives a straightforward access to the first multivalent pyrrolizidine architectures

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6250-6266
DOI: 10.1039/C4OB01117A, PaperGiampiero D'Adamio, Camilla Parmeggiani, Andrea Goti, Antonio J. Moreno-Vargas, Elena Moreno-Clavijo, Inmaculada Robina, Francesca Cardona
The synthesis of the first multivalent pyrrolizidine iminosugars is reported, with up to 9 bioactive molecules on the same scaffold.
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Design and synthesis of (S)- and (R)-[small alpha]-(phenyl)ethylamine-derived NH-type ligands and their application for the chemical resolution of [small alpha]-amino acids

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6239-6249
DOI: 10.1039/C4OB00669K, PaperRyosuke Takeda, Akie Kawamura, Aki Kawashima, Hiroki Moriwaki, Tatsunori Sato, Jose Luis Acena, Vadim A. Soloshonok
A chiral ligand reacts with racemic amino acids to produce easily separable Ni(II) complexes which can be disassembled to afford both enantiomers of target amino acids.
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