Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Synthesis of new unnatural N[small alpha]-Fmoc pyrimidin-4-one amino acids: use of the p-benzyloxybenzyloxy group as a pyrimidinone masking group

25 November, 2014 - 17:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02235A, PaperAbdellatif ElMarrouni, Montserrat Heras
The p-benzyloxybenzyloxy group is used to mask the oxo function of the 4(3H)-pyrimidinone ring in the synthesis of new unnatural amino acids.
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A thermodynamic insight into the recognition of hydrophilic and hydrophobic amino acids in pure water by aza-scorpiand type receptors

25 November, 2014 - 17:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02092H, PaperSalvador Blasco, Begona Verdejo, Carla Bazzicalupi, Antonio Bianchi, Claudia Giorgi, Concepcion Soriano, Enrique Garcia-Espana
Thermodynamic studies about the interaction of scorpiand aza-macrocycles with amino acids in water show entropy driven stabilisations often associated with solvation/desolvation processes.
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One-pot quadruple/triple reaction sequence: a useful tool for the synthesis of natural products

25 November, 2014 - 17:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02143F, PerspectiveK. Kashinath, D. Srinivasa Reddy
Multiple reactions in one pot has always been a useful technique for synthetic organic chemists, as it can minimizes solvent usage, time and the number of purification steps when compared to individual multi-step syntheses.
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Carbocycles from Donor-Acceptor Cyclopropanes

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02117G, Review ArticleHuck K. Grover, Michael R. Emmett, Michael A Kerr
This review summarizes research directed towards the formation of carbocyclic adducts from donor-acceptor cyclopropanes. The focus of the review is on annulation and cycloaddition reactions both inter- and intramolecularly mediated...
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Copper(I) Promoted Cycloalkylation-Peroxidation of Unactivated Alkenes via sp3 C-H Functionalisation

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01962H, CommunicationBhisma K Patel, Arghya Banerjee, Sourav Santra, Aniket Mishra, Nilufa Khatun
A copper (I) promoted cycloalkylation-peroxidation strategy has been developed via a three-component reaction involving cycloalkanes, tert-butyl hydroperoxide (TBHP) and internal conjugated alkene possessing electron-withdrawing groups (EWGs). This process installs C-O...
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Efficient Synthesis of [small alpha]- and [small delta]-Carbolines by Sequential Pd-Catalyzed Site-Selective C-C and Twofold C-N Coupling Reactions

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02226B, PaperTran Quang Hung, Tuan T Dang, Julia Janke, Alexander Villinger, Peter Langer
Two concise and efficient approaches were developed for the synthesis of [small alpha]- and [small delta]-carboline derivatives. The success of the synthesis relies on site-selective Suzuki-Miyaura reaction of 1-chloro-2-bromopyridine or 2,3-dibromopyridine with...
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Catalyst-free synthesis of 2 aryl 1,2 dihydro-quinazolin-4(1H)-thiones from 2 aminobenzothio-amides and aldehydes in water

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02207F, PaperXiao-Feng Wu, Stefan Oschatz, Tom Brunzel, Peter Langer
2-Dihydroquinazolin-4(1H)-thiones were prepared in up to excellent yields from 2-aminobenzothioamides and aldehydes. The reaction is carried out in water without the use of any catalyst or promoter. The sulfur-containing substrate...
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Selective oxygenation of alkynes: a direct approach to diketones and vinyl acetate

25 November, 2014 - 17:17

Org. Biomol. Chem., 2014, 12,9909-9913
DOI: 10.1039/C4OB01404A, PaperXiao-Feng Xia, Zhen Gu, Wentao Liu, Ningning Wang, Haijun Wang, Yongmei Xia, Haiyan Gao, Xiang Liu
Convenient and expedient methods for the synthesis of [small alpha]-diketones and [small beta]-haloenol acetates from arylalkynes using PhI(OAc)2 as an oxidant are developed at room temperature.
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Synthesis and LC-MS/MS analysis of desmosine-CH2, a potential internal standard for the degraded elastin biomarker desmosine

25 November, 2014 - 17:17

Org. Biomol. Chem., 2014, 12,9887-9894
DOI: 10.1039/C4OB01438C, PaperYuko Murakami, Rina Suzuki, Hiroto Yanuma, Jiangtao He, Shuren Ma, Gerard M. Turino, Yong Y. Lin, Toyonobu Usuki
Chemical synthesis and LC-MS/MS analysis of desmosine-CH2, a potential internal standard for the degraded elastin biomarker desmosine, are achieved.
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Gold-catalyzed carboalkoxylations of 2-ethynylbenzyl ethers to form 1- and 3-substituted 2-methoxy-1-H-indenes: Bronsted acids versus gold catalysis

25 November, 2014 - 17:17

Org. Biomol. Chem., 2014, 12,9831-9836
DOI: 10.1039/C4OB01794C, PaperChun-Hao Chen, Chiou-Dong Wang, Yi-Feng Hsieh, Rai-Shung Liu
Selective synthesis of 1- and 3-substituted 2-methoxyindenes from the carboalkoxylations of 2-ethynylbenzyl ethers is described.
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Efficient synthesis of oligosaccharyl 1,2-O-orthoesters from n-pentenyl glycosides and application to the pentaarabinofuranoside of the mycobacterial cell surface

25 November, 2014 - 17:17

Org. Biomol. Chem., 2014, 12,9914-9920
DOI: 10.1039/C4OB01395F, PaperShivaji A. Thadke, Srinivas Hotha
Conversion of n-pentenyl glycosides to glycosyl 1,2-orthoesters that is mild, high yielding, and importantly suitable for oligosaccharide synthesis is identified.
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Radical reactions of borohydrides

25 November, 2014 - 17:17

Org. Biomol. Chem., 2014, 12,9733-9742
DOI: 10.1039/C4OB01784F, Review ArticleTakuji Kawamoto, Ilhyong Ryu
This review article focuses on state-of-the-art borohydride based radical reactions, also covering earlier work, kinetics and some DFT calculations with respect to the hydrogen transfer mechanism.
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Thermodynamic epimeric equilibration and crystallisation-induced dynamic resolution of lobelanine, norlobelanine and related analogues

25 November, 2014 - 17:17

Org. Biomol. Chem., 2014, 12,9797-9810
DOI: 10.1039/C4OB01787K, PaperZ. Amara, G. Bernadat, P.-E. Venot, P. Retailleau, C. Troufflard, E. Drege, F. Le Bideau, D. Joseph
The step-economical synthesis of lobelanine involving a ring closing double aza-Michael (RCDAM) reaction is revisited and successfully extended to the synthesis of various configurationally more stable analogues.
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Selective detection of Al3+ and citric acid with a fluorescent amphiphile

23 November, 2014 - 16:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02095B, PaperZiya Kostereli, Kay Severin
The assembly and disassembly of a fluorescent amphiphile by Al3+ and citrate, respectively, can be used to sense these analytes by fluorescence spectroscopy.
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Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation

23 November, 2014 - 16:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02191F, PaperR. Xu, F. Ali-Rachedi, N. M. Xavier, S. Chambert, F. Ferkous, Y. Queneau, S. J. Cowling, E. J. Davis, J. W. Goodby
The synthesis of glycosteroidal bolaphile biomimics are described along with the liquid-crystalline behaviours as a function of increasing aliphatic composition.
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Palladium(0)-catalyzed synthesis of cyclic glucosides

23 November, 2014 - 16:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB01975J, PaperXin Huang, Chunling Fu, Shengming Ma
A highly regio- and stereo-selective synthesis of cyclic [small beta]-D-glucosides 3via Pd(0)-catalyzed coupling cyclization of allenyl [small beta]-D-glucoside 1 and organic iodides in 20-38% yields is reported.
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The Synthesis of Head-to-Tail Cyclic Sulfono-[gamma]-AApeptides

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02232G, CommunicationHaifan Wu, Fengyu She, Wen-Yang Gao, Austin Prince, Yaqiong Li, Lulu Wei, Allison Mercer, Lukasz Wojtas, Shengqian Ma, Jianfeng cai
We report an efficient method for the preparation of unprecedented head-to-tail cyclic sulfono-[gamma]-AApeptides. Following this method, a number of cyclic sequences bearing two to five subunits were efficiently synthesized. In...
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Direct oxidative coupling of thiols and benzylic ethers via C(sp3)-H activation and C-O cleavage to lead thioesters

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02250E, CommunicationJie Feng, Meifang Lv, Guoping Lu, Chun Cai
An unprecedented C-S formation method via the direct oxidative C(sp3)-H bond functionalization and C-O cleavage of benzylic ethers was developed. Various thioesters including thioester structure containing drug intermediate could be...
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Palladium Catalyzed unactivated [small beta]-methylene C(sp3)-H Bond Alkenylation of Aliphatic Amides and Application in A sequential C(sp3)-H/C(sp2)-H Bond Alkenylation

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02389G, Communicationyu rao, gang shan, guiyi huang
A palladium(II) catalyzed [small beta]-methylene C(sp3)-H bond alkenylation of acyclic aliphatic amides with alkenyl halides has been developed. Both (E)-olefin and (Z)-olefin can be readily accessed by this method and a...
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Unprecedented One-Pot Sequential Thiolate Substitutions of 8-methylthio-BODIPY under Mild Conditions leading to a Red Emissive BODIPY Dye 3,5,8-tris(PhS)-BODIPY.

23 November, 2014 - 16:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01892C, CommunicationKeith Pannell, Alejandro Jose Metta Magana, Eduardo Pena-Cabrera, Robinson Roacho
The simple reaction of phenylthiol with 8-MeS-BODIPY (1) in dichloromethane was readily accomplished to form 8-PhS-BODIPY (2). If the reaction is performed in THF 3,8-bis(phenylthio)-BODIPY (3) and 3,5,8-tris(phenylthio)-BODIPY (4) are...
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