Org. and Biomol. Chem.

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Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-[small alpha]-chloroimines

15 May, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,3393-3405
DOI: 10.1039/C4OB00243A, PaperGert Callebaut, Filip Colpaert, Melinda Nonn, Lorand Kiss, Reijo Sillanpaa, Karl W. Tornroos, Ferenc Fulop, Norbert De Kimpe, Sven Mangelinckx
Mannich-type reactions across N-sulfinyl-[small alpha]-chloroaldimines resulted in syn-stereoselective synthesis of chloroisothreonine derivatives as excellent building blocks.
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Selective synthesis of (Z)-2-enynyl-2-hydroxy-imidazolidine-4,5-diones via Cu(I)-mediated multicomponent coupling of terminal alkynes, carbodiimides and oxalyl chloride

13 May, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,3336-3339
DOI: 10.1039/C4OB00185K, CommunicationFei Zhao, Yuexing Li, Yang Wang, Wen-Xiong Zhang, Zhenfeng Xi
(Z)-2-Enynyl-2-hydroxy-imidazolidine-4,5-diones are synthesized via Cu(I)-mediated (Z)-selective geminal coupling among two terminal alkynes, carbodiimides, and oxalyl chloride. Further transformation is explored.
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Symmetry as a new element to control molecular switches

13 May, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,3371-3379
DOI: 10.1039/C4OB00230J, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Luca Schweighauser, Daniel Haussinger, Markus Neuburger, Hermann A. Wegner
The switching of a tetraazocarbazole macrocycle was investigated and an interdependence of individual azo units was observed depending on their special relationship.
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Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

5 May, 2014 - 15:54

Org. Biomol. Chem., 2014, 12,3201-3210
DOI: 10.1039/C4OB00496E, PaperSteven J. Edeson, Julong Jiang, Stephen Swanson, Panayiotis A. Procopiou, Harry Adams, Anthony J. H. M. Meijer, Joseph P. A. Harrity
UV-Vis spectroscopy offers a convenient and reliable method for alkene stereochemical assignment of 3-acylidene 2-oxindoles.
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Cyclisation reactions of N-cinnamoyl-9-aminoanthracenes

5 May, 2014 - 15:54

Org. Biomol. Chem., 2014, 12,3211-3221
DOI: 10.1039/C4OB00411F, PaperFrank D. King, Abil Aliev, Stephen Caddick, Derek Tocher
N-Cinnamoyl-9-aminoanthracenes cyclise with PPA or triflic acid to form novel 2-azahexacyclo[10.6.6.01,5.06,11.013,18.019,24]tetracosa-6(11),7,9,13,15,17,19(24),20,22-nonaen-3-ones.
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The nature of persistent conformational chirality, racemization mechanisms, and predictions in diarylether heptanoid cyclophane natural products

5 May, 2014 - 15:54

Org. Biomol. Chem., 2014, 12,3303-3309
DOI: 10.1039/C3OB42550A, PaperOmmidala Pattawong, M. Quamar Salih, Nicholas T. Rosson, Christopher M. Beaudry, Paul Ha-Yeon Cheong
Restricted rotations of chemical bonds can lead to the presence of persistent conformational chirality in molecules lacking stereocenters.
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Synthetic routes to the Neuropeptide Y Y1 receptor antagonist 1229U91 and related analogues for SAR studies and cell-based imaging

5 May, 2014 - 15:54

Org. Biomol. Chem., 2014, 12,3271-3281
DOI: 10.1039/C4OB00176A, PaperSimon J. Mountford, Mengjie Liu, Lei Zhang, Marleen Groenen, Herbert Herzog, Nicholas D. Holliday, Philip E. Thompson
The potent Y1 receptor antagonist, 1229U91 has an unusual cyclic dimer structure. We have developed three new routes to the synthesis of analogues. Such variants, including fluorescent conjugates, show potent Y1 antagonism.
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Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3265-3270
DOI: 10.1039/C4OB00234B, PaperSabilla Zhong, Martin Nieger, Angela Bihlmeier, Min Shi, Stefan Brase
An asymmetric synthesis of novel bisindole-piperidine-amino acid hybrids is reported, leading to products with good yields and excellent ees.
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Synthesis and biological evaluation of dual action cyclo-RGD/SMAC mimetic conjugates targeting [small alpha]v[small beta]3/[small alpha]v[small beta]5 integrins and IAP proteins

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3288-3302
DOI: 10.1039/C4OB00207E, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.M. Mingozzi, L. Manzoni, D. Arosio, A. Dal Corso, M. Manzotti, F. Innamorati, L. Pignataro, D. Lecis, D. Delia, P. Seneci, C. Gennari
Dual action cyclo-RGD/SMAC mimetic conjugates endowed with in vitro activity against anti-apoptotic IAPs and pro-angiogenetic integrins are reported.
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Effective catalysis of imine metathesis by means of fast transiminations between aromatic-aromatic or aromatic-aliphatic amines

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3282-3287
DOI: 10.1039/C4OB00107A, PaperMaria Ciaccia, Silvia Pilati, Roberta Cacciapaglia, Luigi Mandolini, Stefano Di Stefano
Transiminations involving aromatic or aliphatic amines were found to be fast enough to be effectively employed in the catalysis of imine metathesis.
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Nucleophilic addition to N-alkoxyamides

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3147-3150
DOI: 10.1039/C4OB00389F, PerspectiveTakaaki Sato, Noritaka Chida
Amide-selective nucleophilic addition using N-alkoxyamides minimized extra protecting group manipulations and redox reactions, resulting in the concise total synthesis of gephyrotoxin.
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Inverse solvent effects in the heterogeneous and homogeneous epoxidation of cis-2-heptene with [2-percarboxyethyl]-functionalized silica and meta-chloroperbenzoic acid

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3246-3250
DOI: 10.1039/C4OB00253A, PaperRossella Mello, Jeymy T. Sarmiento-Monsalve, Diana Vargas-Oviedo, Rafael Acerete, Maria Elena Gonzalez-Nunez, Gregorio Asensio
The organized solvent layer on the solid surface determines the reaction rate in the heterogeneous epoxidation of cis-2-heptene.
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Cooperative hydrolysis of aryl esters on functionalized membrane surfaces and in micellar solutions

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3175-3180
DOI: 10.1039/C4OB00247D, PaperM. Poznik, B. Konig
Catalytic hydrolysis of peptides, proteins, phosphates or carboxylate esters in nature is catalysed by enzymes, which are efficient, fast and selective.
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Convergent routes to substituted naphthylamides

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3251-3264
DOI: 10.1039/C4OB00339J, PaperNgoc Diem My Tran, Samir Z. Zard
Substituted 1- and 2-naphthylamides can be obtained by the radical addition-cyclisation of amido-containing phenacyl xanthates to vinyl pivalate followed by acid catalysed aromatisation.
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Synthesis of new anionic carbosilane dendrimers via thiol-ene chemistry and their antiviral behaviour

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3222-3237
DOI: 10.1039/C4OB00162A, PaperMarta Galan, Javier Sanchez Rodriguez, Jose Luis Jimenez, Miguel Relloso, Marek Maly, F. Javier de la Mata, M. A. Munoz-Fernandez, Rafael Gomez
Thiol-ene chemistry, enable the identification of anionic carbosilane dendrimers as readily available, good and safe candidates for vaginal microbicides against HIV.
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Synthesis and evaluation of monophosphoryl lipid A derivatives as fully synthetic self-adjuvanting glycoconjugate cancer vaccine carriers

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3238-3245
DOI: 10.1039/C4OB00390J, PaperZhifang Zhou, Mohabul Mondal, Guochao Liao, Zhongwu Guo
Monophosphoryl lipid A derivatives were used as both carrier molecules and built-in adjuvants to create fully synthetic self-adjuvanting glycoconjugate cancer vaccines.
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"Click and go": simple and fast folic acid conjugation

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3181-3190
DOI: 10.1039/C4OB00150H, PaperAlexandre F. Trindade, Raquel F. M. Frade, Ermelinda M. S. Macoas, Catia Graca, Catarina A. B. Rodrigues, Jose M. G. Martinho, Carlos A. M. Afonso
A novel approach for conjugation of folic acid is presented allowing for its quantitative conjugation with several types of molecules (fluorescent probes) and materials (polymers and silica) based on strain-promoted alkyne-azide cycloaddition, without the need for expensive chromatographic purifcation.
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Total synthesis of lycorine-type alkaloids by cyclopropyl ring-opening rearrangement

29 April, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,3191-3200
DOI: 10.1039/C4OB00126E, PaperDandan Liu, Long Ai, Fan Li, Annan Zhao, Jingbo Chen, Hongbin Zhang, Jianping Liu
Anhydrocaranine, [gamma]-lycorane and putative amarbellisine were synthesized based on a series reactions including a novel cyclopropyl ring-opening rearrangement.
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N,N[prime or minute]-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea: a privileged motif for catalyst development

29 April, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,3151-3162
DOI: 10.1039/C4OB00306C, Review ArticleZhiguo Zhang, Zongbi Bao, Huabin Xing
This review summarizes the key developments of N,N[prime or minute]-bis[3,5-bis(trifluoromethyl)phenyl]thiourea (Schreiner's thiourea)-mediated reactions with the aim to further expand the applications of (thio)urea-based catalysts.
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The development of catalytic nucleophilic substitution reactions: challenges, progress and future directions

29 April, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,2993-3003
DOI: 10.1039/C4OB00032C, Review ArticleJie An, Ross M. Denton, Tristan H. Lambert, Eric D. Nacsa
Bimolecular nucleophilic substitution reactions of alcohols are fundamentally important transformations in organic chemistry yet, to date, they are relatively underdeveloped with respect to catalysis.
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