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Rapid formation of complexity in organic synthesis
28 October 2009
Chem Soc Rev issue 11 is a thematic issue illustrating the current state-of-the-art in natural product total synthesis guested edited by Huw Davies and Erik Sorensen
Issue 23 of OBC
12 November 2009
Find out more about the cutting edge research featured in the latest issue
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Contents list for Organic & Biomolecular Chemistry, issue 23, 2009
Front cover
Org. Biomol. Chem., 2009, 7, 4801
DOI: 10.1039/B922537B
Inside front cover
Org. Biomol. Chem., 2009, 7, 4802
DOI: 10.1039/B922538M
Contents and Highlights in Chemical Biology
Org. Biomol. Chem., 2009, 7, 4803
DOI: 10.1039/B922539K
Communications
Cationic rhodium(I)/bisphosphine complex-catalyzed cyclization of 1,6-diynes with carboxylic acids
Ken Tanaka, Shunsuke Saitoh, Hiromi Hara and Yu Shibata,
Org. Biomol. Chem., 2009, 7, 4817
DOI: 10.1039/b913344e
A cationic rhodium(I)/bisphosphine complex catalyzes carboxylative cyclizations of 1,6-diynes, leading to cyclic dienyl carboxylates, in high yields with high chemo-, regio-, and stereoselectivities under mild reaction conditions.
Microwave-assisted versatile hydrogenation of carbonyl compounds using supported metal nanoparticles
Maria Jose Gracia, Juan Manuel Campelo, Elia Losada, Rafael Luque, Jose Maria Marinas and Antonio Angel Romero,
Org. Biomol. Chem., 2009, 7, 4821
DOI: 10.1039/b913695a
An efficient microwave-assisted hydrogenation of carbonyl compounds was performed using supported Pt and Pd nanoparticles on Al-SBA-15 materials where excellent conversions and selectivities were achieved in very short times of reaction (5-30 min).
The pyridinone-methide elimination
Rotem Perry-Feigenbaum, Phil S. Baran and Doron Shabat,
Org. Biomol. Chem., 2009, 7, 4825
DOI: 10.1039/b915265b
This study presents the first demonstration of a pyridinone-methide elimination. This elimination could be applied as an applicable tool in designing self-immolative linkers.
Stereodivergent syntheses at the glucose backbone
Jian Yin and Torsten Linker,
Org. Biomol. Chem., 2009, 7, 4829
DOI: 10.1039/b918893m
R or S– that is the point: Starting from 2-C-branched carbohydrate 1, each of the two diastereotopic ester groups was selectively replaced by methyl, OH, and NH2 groups. Such stereodivergent syntheses afforded products 2 in good yields and excellent stereoselectivities in only a few steps.
Papers
Synthesis of unsaturated phosphatidylinositol 4,5-bisphosphate and analogues
Nitesh Panchal and Piers R. J. Gaffney,
Org. Biomol. Chem., 2009, 7, 4832
DOI: 10.1039/b907551h
A myo-inositol triacetal building block was elaborated to unsaturated Ptdlns(4,5)P2 and acetylenic analogues including phosphorothioates.
Neighbouring group participation vs. addition to oxacarbenium ions: studies on the synthesis of mycobacterial oligosaccharides
Susanne A. Stalford, Colin A. Kilner, Andrew G. Leach and W. Bruce Turnbull,
Org. Biomol. Chem., 2009, 7, 4842
DOI: 10.1039/b914417j
A bicyclic sulfonium ion based on the mycobacterial sugar MTX can react via SN1 or SN2 pathways to yield glycoside products.
Palladium-catalysed ortho-arylation of carbamate-protected phenols
Robin B. Bedford, Ruth L. Webster and Charlotte J. Mitchell,
Org. Biomol. Chem., 2009, 7, 4853
DOI: 10.1039/b916724m
The carbamate group proves to be an excellent directing group for the palladium-catalysed CH arylation of protected phenols.
Lewis acid InBr3-catalyzed arylation of diorgano diselenides and ditellurides with arylboronic acids
Kai Ren, Min Wang and Lei Wang,
Org. Biomol. Chem., 2009, 7, 4858
DOI: 10.1039/b914533h
A high yield Lewis acid InBr3-catalyzed direct cross-coupling reaction of arylboronic acids with diorgano diselenides and ditellurides without any additive has been developed.
The coumarin
indole transformation—a method for preparing 4-halo-5-hydroxyindoles from coumarins
Elia J. L. Stoffman and Derrick. L. J. Clive,
Org. Biomol. Chem., 2009, 7, 4862
DOI: 10.1039/b914580j
Readily accessible 3-alkoxycarbonyl-6-hydroxy-5-halocoumarins can be converted into 4-halo-5-hydroxyindoles; such compounds are not very easily accessed by current methodology
Direct synthesis of sulfonated azacalixarenes in water
Jonathan Clayden, Stephen J. M. Rowbottom, Warren J. Ebenezer and Michael G. Hutchings,
Org. Biomol. Chem., 2009, 7, 4871
DOI: 10.1039/b911631a
Azacalixarene structures form in water by simple sequential reaction of cyanuric chloride with sulfonated diamines and amines.
Synthesis and X-ray structural analysis of platinum and ethynyl-platinum corannulenes: supramolecular tectons
Roman Maag, Brian H. Northrop, Anna Butterfield, Anthony Linden, Oliver Zerbe, Young Min Lee, Ki-Whan Chi, Peter J. Stang and Jay S. Siegel,
Org. Biomol. Chem., 2009, 7, 4881
DOI: 10.1039/b916020e
Direct platination of chloro and TMSethynyl corannulenes leads to new supramolecular tectons.
Evaluation of the pharmacophoric motif of the caged Garcinia xanthones
Oraphin Chantarasriwong, Woo Cheal Cho, Ayse Batova, Warinthorn Chavasiri, Curtis Moore, Arnold L. Rheingold and Emmanuel A. Theodorakis,
Org. Biomol. Chem., 2009, 7, 4886
DOI: 10.1039/b913496d
A Pd(0)-catalyzed reverse prenylation of catechols was developed that, in combination with a Claisen/Diels–Alder reaction cascade, provides rapid and efficient access to various caged Garcinia xanthones, such as cluvenone ( 7). This motif represents a promising lead for the development of new chemotherapeutic agents.
Synthesis and kinetic studies of a low-molecular weight organocatalyst for phosphate hydrolysis in water
Michael Merschky and Carsten Schmuck,
Org. Biomol. Chem., 2009, 7, 4895
DOI: 10.1039/b914974k
Compound 1, containing two histidines and an oxoanion binding site, efficiently hydrolyzes phosphates in aqueous buffer with rate enhancements of up to two orders of magnitude.
Calix[4]arenes featuring a direct lower rim attachment of dansyl groups. Synthesis, fluorescence properties and first report on crystal structures
Tobias Gruber, Conrad Fischer, Marika Felsmann, Wilhelm Seichter and Edwin Weber,
Org. Biomol. Chem., 2009, 7, 4904
DOI: 10.1039/b911800d
Synthesis, crystal structures and fluorescent chemosensing capability for metal ions of new calix[4]arenes featuring a direct lower rim attachment mode of dansyl groups are reported.
Peptide thioester synthesis through NS acyl-transfer: application to the synthesis of a 
-defensin
Jaskiranjit Kang, Natalie L. Reynolds, Christine Tyrrell, Julia R. Dorin and Derek Macmillan,
Org. Biomol. Chem., 2009, 7, 4918
DOI: 10.1039/b913886b
Peptide thioesters readily prepared through NS acyl-transfer provide access to biologically active mini-proteins.
4-Aminoproline-based arginine-glycine-aspartate integrin binders with exposed ligation points: practical in-solution synthesis, conjugation and binding affinity evaluation
Lucia Battistini, Paola Burreddu, Paola Carta, Gloria Rassu, Luciana Auzzas, Claudio Curti, Franca Zanardi, Leonardo Manzoni, Elena M. V. Araldi, Carlo Scolastico and Giovanni Casiraghi,
Org. Biomol. Chem., 2009, 7, 4924
DOI: 10.1039/b914836a
A practical in-solution synthesis of new 4-aminoproline-based RGD cyclic tetrapeptides is presented. Remarkable nanomolar 
V3 and V5 integrin binding affinities were found for all synthesized compounds.
Synthetic routes to pyrrolizine-1,5-dione derivatives by flash vacuum pyrolysis of amidomethylene derivatives of Meldrum's acid
Hamish McNab, Mark Morrow, Simon Parsons, David A. Shannon and Kirsti Withell,
Org. Biomol. Chem., 2009, 7, 4936
DOI: 10.1039/b911951e
Methoxymethylene Meldrum's acid reacts with lactams in refluxing acetonitrile to give N-substituted amidomethylene products. Flash vacuum pyrolysis of such derivatives containing a pyrrolidinone ring provides pyrrolizinediones. The constitution of the products at each stage of the sequence is supported by X-ray crystal structures.
L-Proline-catalyzed synthesis of highly functionalized multisubstituted 1,4-dihydropyridines
Huanfeng Jiang, Ronghuan Mai, Hua Cao, Qiuhua Zhu and Xiaohang Liu,
Org. Biomol. Chem., 2009, 7, 4943
DOI: 10.1039/b914659h
Highly functionalized multisubstituted 1,4-dihydropyridines 5 have been concisely synthesized in moderate to good yields viaL-proline-catalyzed one-pot multicomponent reactions (MCRs) of alkynoates or alkynones 1, amines 2, 
-dicarbonyl compounds 3 and aldehydes 4 under mild conditions.
Synthesis of a photo-caged aminooxy alkane thiol
Rock J. Mancini, Ronald C. Li, Zachary P. Tolstyka and Heather D. Maynard,
Org. Biomol. Chem., 2009, 7, 4954
DOI: 10.1039/b904195h
A photo-caged aminooxy alkane thiol was synthesized, used to form a self-assembled monolayer on gold, deprotected and subsequently conjugated to a ketone-containing small molecule.
Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation
Kevin M. Allan, Boram D. Hong and Brian M. Stoltz,
Org. Biomol. Chem., 2009, 7, 4960
DOI: 10.1039/b913336d
A method for the rapid synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from -ketoesters using a one-pot procedure involving aryne acyl-alkylation followed either by condensation with ammonia or intramolecular condensation and aerobic oxidation is described.
Photolabile N-hydroxypyrid-2(1H)-one derivatives of guanine nucleosides: a new method for independent guanine radical generation
Panagiotis Kaloudis, Cecilia Paris, Despoina Vrantza, Susana Encinas, Raul Pérez-Ruiz, Miguel A. Miranda and Thanasis Gimisis,
Org. Biomol. Chem., 2009, 7, 4965
DOI: 10.1039/b909138f
An alternative approach for the site specific, independent generation of the guanine radical, using N-hydroxypyrid-2(1H)-one as a photolabile modifier of guanine, is proposed. Novel derivatives capable of generating the neutral guanine radical (G(-H)
) upon photolysis were synthesized and characterized.
Synthesis of new, UV-photoactive dansyl derivatives for flow cytometric studies on bile acid uptake
Jana Rohacova, M. Luisa Marin, Alicia Martínez-Romero, José-Enrique O'Connor, M. Jose Gomez-Lechon, M. Teresa Donato, Jose V. Castell and Miguel A. Miranda,
Org. Biomol. Chem., 2009, 7, 4973
DOI: 10.1039/b912134j
Four new fluorescent derivatives of cholic acid have been synthesized incorporating a dansyl moiety at 3-, 3-, 7- or 7- positions. They are UV photoactive and also exhibit green fluorescence and have been demonstrated to be suitable for kinetic transport studies.
Structural analysis of the DNA target site and its interaction with Mbp1
Anna V. Chernatynskaya, Lynn Deleeuw, John O. Trent, Tom Brown and Andrew N. Lane,
Org. Biomol. Chem., 2009, 7, 4981
DOI: 10.1039/b912309a
We developed a novel approach to docking flexible high-resolution DNA and protein structures using indirect experimental data that rationalizes available mutational data. The image shows a model of the Mbp1:DNA complex – DNA is in green, and red indicates the binding site of the protein.
Thermal melting studies of alkyne- and ferrocene-containing PNA bioconjugates
Anna M. Sosniak, Gilles Gasser and Nils Metzler-Nolte,
Org. Biomol. Chem., 2009, 7, 4992
DOI: 10.1039/b913964h
Thermal melting studies of PNA oligomers containing either a terminal or an internal incorporated 
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ferrocene moiety with a range of DNA strands have been investigated.
Synthesis and stereochemical determination of batzelladine C methyl ester
Michael Butters, Christopher D. Davies, Mark C. Elliott, Joseph Hill-Cousins, Benson M. Kariuki, Li-ling Ooi, John L. Wood and Stuart V. Wordingham,
Org. Biomol. Chem., 2009, 7, 5001
DOI: 10.1039/b914744f
The two possible epimers of batzelladine C methyl ester have been prepared using a diastereoselective three-component coupling reaction as a key step. The stereochemistry of the natural product has therefore been established.
Synthesis of novel synthetic intermediates from the reaction of benzimidazole and triazole carbenes with ketenimines and their application in the construction of spiro-pyrroles
Jun-Ming Mo, Yang-Guang Ma and Ying Cheng,
Org. Biomol. Chem., 2009, 7, 5010
DOI: 10.1039/b915215f
The reaction of benzimidazole and triazole carbenes with ketenimines provided novel synthons for the construction of multifunctional spiro-pyrroles.
Synthesis of non-proteinogenic phenylalanine derivatives by rhodium-catalyzed [2+2+2] cycloaddition reactions
Lídia Garcia, Anna Pla-Quintana and Anna Roglans,
Org. Biomol. Chem., 2009, 7, 5020
DOI: 10.1039/b910961g
Rh(I)-catalyzed [2+2+2] cycloaddition reactions have been efficiently performed on propargylglycine amino acids and diversely substituted diynes to yield non-proteinogenic phenylalanine derivatives.
Component match in rhodium catalyzed three-component reactions of ethyl diazoacetate, H2O and aryl imines: a highly diastereoselective one-step synthesis of -aryl isoserine derivatives
Zhenqiu Guo, Taoda Shi, Jun Jiang, Liping Yang and Wenhao Hu,
Org. Biomol. Chem., 2009, 7, 5028
DOI: 10.1039/b915013g
Three-component reactions of ethyl diazoacetate, H2O and aryl imines affords a highly diastereoselective one-step synthesis of -aryl isoserine derivatives.
Back matter
Org. Biomol. Chem., 2009, 7, 5034
DOI: 10.1039/B922546N
Back cover
Org. Biomol. Chem., 2009, 7, 5035
DOI: 10.1039/B922545P
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