RSC - Org. Biomol. Chem. latest articles

Asymmetric Michael addition to [gamma]-hydroxy-[small alpha],[small beta]-unsaturated aldehyde with boronic acids catalyzed by resin-supported peptide

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25431J, Communication

Kengo Akagawa, Masahide Sugiyama, Kazuaki Kudo
A resin-supported peptide catalyst effective for the asymmetric Michael addition to (E)-4-hydroxybut-2-enal with boronic acids was developed. From a spectral study, it was revealed that the optimum peptide consisited of...
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FeCl3 Promoted Highly Regioselective [3+2] Cycloaddition of Dimethyl 2-Vinyl and Aryl Cyclopropane-1,1-dicarboxylates with Aryl Isothiocyanates。

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25682G, Communication

Hao Li, Wei Wang, Hong Liu, Huina Wang, Wei Yang
A FeCl3 promoted [3+2] annulation of dimethyl 2-vinyl and arylcyclopropane-1,1-dicarboxylate with aryl isothiocyanates has been developed to give pyrrolidine-2-thiones in good yields and in a highly regioselective manner.
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Assisted tandem catalytic RCM-aromatization in the synthesis of pyrroles and furans

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25543J, Paper

Bernd Schmidt, Stefan Krehl, Eric Jablowski
Pyrroles and furans are available from diallyl amines and diallyl ethers, respectively, via an assisted tandem catalytic approach.
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Hydrogen bond-assisted macrocyclic oligocholate transporters in lipid membranes

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25301A, Paper

Lakmini Widanapathirana, Xueshu Li, Yan Zhao
The carboxylic acid dimer interactions helped the amphiphilic oligocholate macrocycles stack into nanopores in lipid bilayer membranes.
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Structural diversity in native cyclodextrins/folic acid complexes - from [2] rotaxane to exclusion compound

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25683E, Communication

Magdalena Ceborska, Magdalena Zimnicka, Mariusz Pietrzak, Anna Troc, Malgorzata Kozbial, Janusz Lipkowski
The formation of different complexes of folic acid depending on the size of host cyclodextrin resulting in either exclusion compound (with the smallest [small alpha]-cyclodextrin) or 2-rotaxane, where cyclodextrin is threaded...
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Non-covalent interactions of coumarin dyes with cucurbit[7]uril macrocycle: modulation of ICT to TICT state conversion

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25759A, Paper

Nilotpal Barooah, Jyotirmayee Mohanty, Haridas Pal, Achikanath C. Bhasikuttan
Enhanced fluorescence yield and increased aqueous solubility of coumarin dyes on cucurbituril encapsulation as promising system for aqueous dye laser and cellular imaging.
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One-pot synthesis of 2-aminoquinoline-based alkaloids from acetonitrile

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25709B, Paper

Takashi Tomioka, Yusuke Takahashi, Toshihide Maejima
[small alpha]-Diaminoboryl carbanions, readily prepared from acetonitrile, stereoselectively convert 2-nitrobenzaldehydes into nitrophenyl (Z)-acrylonitriles. Subsequent reductive cyclization leads to a series of 2-aminoquinoline derivatives. The entire procedure is practically operated in a single flask.
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Possible cage-like nanostructures formed by amino acids

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25558H, Paper

Cui-hong Wang, Qi Wu, Wen-jie Fan, Rui-qin Zhang, Zijing Lin
The figure shows the cage-like nanostructure formed by serine decamers and its application in encapsulating a C₂₀ molecule. The cage-like nanostructure is expected to have important applications in drug delivery.
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Very high stereoselectivity in organocatalyzed desymmetrizing aldol reactions of 3-substituted cyclobutanones

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25813G, Paper

David J. Aitken, Angela M. Bernard, Francesca Capitta, Angelo Frongia, Regis Guillot, Jean Ollivier, Pier Paolo Piras, Francesco Secci, Marco Spiga
N-Phenylsulfonyl (S)-proline catalyzes the direct aldol reaction of 3-substituted cyclobutanones and aryl aldehydes with excellent diastereoselectivity and enantioselectivity.
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Catalytic activity of halohydrin dehalogenases towards spiroepoxides

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25470K, Paper

Maja Majeric Elenkov, Ines Primozic, Tomica Hrenar, Ana Smolko, Irena Dokli, Branka Salopek-Sondi, Lixia Tang
High regioselectivities and moderate to high enantioselectivities were found in the azidolysis of spiroepoxides catalysed by halohydrin dehalogenases.
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Synthesis of pyrido[2,3-b]indoles and pyrimidoindoles via Pd-catalyzed amidation and cyclization

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25371B, Paper

Arepalli Sateesh Kumar, P. V. Amulya Rao, Rajagopal Nagarajan
Synthesis of pyrido[2,3-b]indoles and pyrimidoindoles via Pd-catalyzed amidation and cyclization.
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Exploring the trifluoromenadione core as a template to design antimalarial redox-active agents interacting with glutathione reductase

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25229E, Paper

Don Antoine Lanfranchi, Didier Belorgey, Tobias Muller, Herve Vezin, Michael Lanzer, Elisabeth Davioud-Charvet
Elimination of the CF₃ group at the core of trifluoromenadione was investigated as a potential antimalarial multi-dual drug action. The trifluoromenadione bearing the alkyl side-chain of atovaquone was revealed as an effective mechanism-based inhibitor of glutathione reductase leading to potent antimalarial effects.
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Generation of molecular complexity from cyclooctatetraene using dienyliron and olefin metathesis methodology

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25636C, Communication

Mohamed F. El-Mansy, Anobick Sar, Subhabrata Chaudhury, Nathaniel J. Wallock, William A. Donaldson
Complex molecular architectures are created in 5-6 steps from the simple hydrocarbon cyclooctatetraene.
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Synthesis and evaluation of atropos dihydro-5H-dibenzazepinium halide PTCs derived from [small alpha]-methylbenzylamine

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25437A, Paper

Barry Lygo, Umar Butt, Maria Cormack
A short synthetic route to diastereoisomeric atropos dihydro-5H-dibenz[c,e]azepinium salts via reaction of a single enantiomer of (R)-[small alpha]-methylbenzylamine with a racemic atropos biphenol derivative is described.
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Synthesis of an unusual dinuclear chiral iron complex and its application in asymmetric hydrophosphorylation of aldehydes

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25810B, Communication

Pandi Muthupandi, Govindasamy Sekar
An unusual dinuclear chiral iron complex has been synthesized and effectively utilized in the asymmetric hydrophosphorylation of aldehydes to synthesize optically active [small alpha]-hydroxy phosphonates with excellent yield and good enantioselectivity.
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The effects of solvent on switchable stereoselectivity: copper-catalyzed asymmetric conjugate additions using D2-symmetric biphenyl phosphoramidite ligands

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25730K, Paper

Han Yu, Fang Xie, Zhenni Ma, Yangang Liu, Wanbin Zhang
A highly enantioselective copper-catalyzed conjugate addition of diethylzinc to acyclic aromatic enones was developed, which demonstrated that toluene and THF respectively as solvent can completely reverse the absolute configuration of the products.
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Study of N1-alkylation of indoles from the reaction of 2(or 3)-aminoindole-3-(or 2)carbonitriles with DMF-dialkylacetals

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25747E, Paper

Yvonnick Loidreau, Sigismund Melissen, Vincent Levacher, Cedric Loge, Jerome Graton, Jean-Yves Le Questel, Thierry Besson
DMF-dialkoxyacetals allowed the appearance of reactive alkoxyiminium species for convenient access to indole precursors of various building blocks.
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Highly efficient intramolecular Cannizzaro reaction between 1,3-distal formyl groups at the upper rim of a cone-calix[4]arene

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25458A, Paper

Marzia Galli, Jose Augusto Berrocal, Stefano Di Stefano, Roberta Cacciapaglia, Luigi Mandolini, Laura Baldini, Alessandro Casnati, Franco Ugozzoli
A very efficient intramolecular hydride transfer allows a facile desymmetrization of 1,3-distal diformylated calix[4]arenes.
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A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25514F, Paper

Milena V. Trmcic, Radomir V. Matovic, Gordana I. Tovilovic, Biljana Z. Ristic, Vladimir S. Trajkovic, Zorana B. Ferjancic, Radomir N. Saicic
The C,D-spirolactone is the first paclitaxel analogue without an oxetane ring that shows significant cytotoxicity, and acts by autophagy, not apoptosis.
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Synthesis and evaluation of novel caged DNA alkylating agents bearing 3,4-epoxypiperidine structure

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25366F, Paper

Yuji Kawada, Tetsuya Kodama, Kazuyuki Miyashita, Takeshi Imanishi, Satoshi Obika
Novel caged DNA alkylating agents, 3,4-epoxypiperidine derivatives, showed various degrees of bioactivity depending on the photosensitivity of the protecting groups.
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Polystyrene-supported TBD catalyzed ring-opening of N-tosylaziridines with silylated nucleophiles

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25435B, Paper

Satoru Matsukawa, Takeru Harada, Shiori Yasuda
Polystyrene-supported TBD (PS-TBD) catalyzes the ring-opening of N-tosylaziridines with silylated nucleophiles to give the corresponding products in high yields. PS-TBD was easily recovered and reused without significant loss of catalytic activity.
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Direct catalytic asymmetric synthesis of highly functionalized (2-ethynylphenyl)alcohols via Barbas-List aldol reaction: scope and synthetic applications

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25563D, Paper

Dhevalapally B. Ramachary, Rumpa Mondal, R. Madhavachary
A general approach to high-yielding asymmetric synthesis of (2-ethynylphenyl)alcohols as synthons in medicinal chemistry was achieved through Barbas-List aldol reaction on ketones with 2-alkynylbenzaldehydes in the presence of a catalytic amount of trans-4-OH-L-proline or L-prolinamide derivative.
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Dipicolylamine as a unique structural switching element for helical peptides

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB07118E, Paper

Yusuke Azuma, Haruka Imai, Tomoyuki Yoshimura, Takeo Kawabata, Miki Imanishi, Shiroh Futaki
A simple method for on-resin synthesis of dipicolylamine (Dpa)-containing peptides was developed, which enables the design of a unique metal-responsive peptide.
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Sequential approach to the synthesis of 'U and Z' shaped polycyclic heteroarenes

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25173F, Paper

Hardesh K. Maurya, Sanjay K. Gautam, Ramendra Pratap, Vishnu K. Tandon, Abhinav Kumar, Vikas Bajpai, Brijesh Kumar, Vishnu Ji Ram
The synthesis of three new classes of heteroarenes, built through the sequential fusion of naphthalene, benzo/naphtho[b]oxepine and thiochromene rings with pyran and pyrimidine rings, and giving 'U and Z' shaped structural frameworks is reported.
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Vinyl-triphenylamine dyes, a new family of switchable fluorescent probes for targeted two-photon cellular imaging: from DNA to protein labeling

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25515D, Paper

Blaise Dumat, Guillaume Bordeau, Ana I. Aranda, Florence Mahuteau-Betzer, Yara El Harfouch, Germain Metge, Fabrice Charra, Celine Fiorini-Debuisschert, Marie-Paule Teulade-Fichou
A new family of nonlinear fluorescent probes for specific DNA or protein labeling was designed by structure space exploration around the vinyl-triphenylamine core.
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A click chemistry route to 2-functionalised PEGylated and cationic [small beta]-cyclodextrins: co-formulation opportunities for siRNA delivery

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25490E, Paper

Aoife M. O'Mahony, Julien Ogier, Stephane Desgranges, John F. Cryan, Raphael Darcy, Caitriona M. O'Driscoll
Cuprous-catalysed 'click' chemistry was employed to synthesise cationic and PEGylated amphiphilic cyclodextrins. These cyclodextrins were co-formulated and investigated for siRNA delivery.
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Precipitation-driven self-sorting of imines

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25736J, Communication

Rio Carlo Lirag, Karolina Osowska, Ognjen S. Miljanic
Judicious choice of precipitation conditions can lead to self-sorting of equilibrating mixtures of aromatic aldehydes and substituted anilines into a handful of imine products. The selectivity of this process is...
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Imidazo[1,5-a]pyridine-1-ylalkylalcohols: synthesis via intramolecular cyclization of N-thioacyl 1,2-aminoalcohols and their silyl ethers and molecular structures

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25438G, Paper

Toshiaki Murai, Eri Nagaya, Fumitoshi Shibahara, Toshifumi Maruyama
Iodine-mediated cyclization of N-thioacyl 1,2-aminoalcohols and their silyl ethers was complete within 30 min to give imidazo[1,5-a]pyridine derivatives.
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Synthesis of the trans-hydrindane core of dictyoxetane

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25384D, Paper

Benedicte Defaut, Thomas B. Parsons, Neil Spencer, Louise Male, Benson M. Kariuki, Richard S. Grainger
Preparation of the trans-hydrindane core of the marine natural product dictyoxetane is reported for the first time. A phosphorane-mediated, pinacol-like rearrangement is used to establish the requisite trans ring junction.
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Supramolecular polymerization of oligopyrenotides - stereochemical control by single, natural nucleotides

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25320H, Paper

Alina L. Nussbaumer, Florent Samain, Vladimir L. Malinovskii, Robert Haner
The formation of supramolecular polymers from oligopyrenotides can be controlled by chiral auxiliaries, such as natural nucleotides. The supramolecular polymerization process exhibits a high degree of amplification of chirality. Depending on the nature of the nucleotide, the helical sense of the polymers is shifted to either an M-helix or a P-helix.
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Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25554E, Paper

Floris Chevallier, Thomas Blin, Elisabeth Nagaradja, Frederic Lassagne, Thierry Roisnel, Yury S. Halauko, Vadim E. Matulis, Oleg A. Ivashkevich, Florence Mongin
2-Aryl-1,2,3-triazoles have been synthesized and deproto-metallated using a 2,2,6,6-tetramethylpiperidino-based lithium-zinc combination. The outcome of the reactions has been discussed in the light of DFT calculated CH acidities (THF solution).
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Investigation of asymmetric alcohol dehydrogenase (ADH) reduction of acetophenone derivatives: effect of charge density

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06870B, Paper

Hemantkumar G. Naik, Bahar Yeniad, Cor E. Koning, Andreas Heise
In an effort to study the effect of substituent groups of the substrate on the alcohol dehydrogenase (ADH) reductions of aryl-alkyl ketones, several derivatives of acetophenone have been evaluated against ADHs from Lactobacillus brevis and Thermoanaerobacter sp.
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Design, synthesis and binding studies of a novel quadruple ADDA hydrogen-bond array

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25333J, Paper

Maria L. Pellizzaro, Simon A. Barrett, Julie Fisher, Andrew J. Wilson
This paper describes the synthesis and molecular recognition properties of a new quadruple hydrogen-bonding array: ureidodiimidazole (UDIM).
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Design and synthesis of a novel class of CK2 inhibitors: application of copper- and gold-catalysed cascade reactions for fused nitrogen heterocycles

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25298H, Paper

Yamato Suzuki, Shinya Oishi, Yoshinori Takei, Misato Yasue, Ryosuke Misu, Saori Naoe, Zengye Hou, Tatsuhide Kure, Isao Nakanishi, Hiroaki Ohno, Akira Hirasawa, Gozoh Tsujimoto, Nobutaka Fujii
A series of fused nitrogen heterocycles for novel CK2 inhibitors were designed and synthesized via copper- and gold-catalysed cascade/multicomponent reactions as key steps.
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Porphyrin-templated synthetic G-quartet (PorphySQ): a second prototype of G-quartet-based G-quadruplex ligand

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25601K, Paper

Hai-Jun Xu, Loic Stefan, Romain Haudecoeur, Sophie Vuong, Philippe Richard, Franck Denat, Jean-Michel Barbe, Claude P Gros, David Monchaud
Template-assembled synthetic G-quartet (TASQ) has been reported recently as G-quadruplex ligands interacting with DNA according to an unprecedented, nature-inspired 'like likes like' approach, based on the association between two G-quartets,...
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A chemosensor for dihydrogenphosphate based on an oxoazamacrocycle possessing three thiourea arms

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25498K, Paper

Anxela Aldrey, Alejandro Alberto Macias, Rufina M Bastida, Guillermo Zaragoza, Gustavo Rama, Miguel Vazquez Lopez
A new H-bond macrocyclic chemosensor in organic media is reported. This system displayed marked changes in the UV-Vis spectra and showed selectivity for dihydrogenphosphate over other inorganic anions, such as...
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Site-Specific Protein Propargylation Using Tissue Transglutaminase

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25752A, Paper

Claudio Gnaccarini, Wajih Ben-Tahar, Amina Mulani, Isabelle Roy, William D Lubell, Joelle Pelletier, Jeffrey W Keillor
Transglutaminases (TGases) catalyse the transamidation of glutamine residues with primary amines. Herein we report the first FRET-based activity assay for the direct detection of the ligation (transamidation) reaction mediated by...
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An enzyme-initiated Smiles rearrangement enables the development of an assay of MshB, the GlcNAc-Ins deacetylase of mycothiol biosynthesis

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25429H, Paper

Dirk Antonie Lamprecht, Ndivhuwo Olga Muneri, Hayden Eastwood, Kevin Jonathan Naidoo, Erick Strauss, Anwar Jardine
MshB is the N-acetyl-1-D-myo-inosityl-2-amino-2-deoxy-D-glucopyranoside (GlcNAc-Ins) deacetylase active as one of the enzymes involved in the biosynthesis of mycothiol (MSH), a protective low molecular weight thiol present only in Mycobacterium tuberculosis...
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Long conjugated 2-nitrobenzyl derivatives caged anticancer prodrugs with visible light regulated release: preparation and functionalizations

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25701G, Paper

Chunyan Bao, Ming Jin, Bo Li, Yaodong Xu, Jingyan Jin, Linyong Zhu
A series of anticancer prodrugs with different chemical functional groups were prepared, in which the styryl conjugated 2-nitrobenzyl derivatives were introduced as the phototrigger to regulate the drug (chlorambucil) release....
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Synthesis of isoxazoles en route to semi-aromatized polyketides: dehydrogenation of benzonitrile oxide-para-quinone acetal cycloadducts

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25423A, Paper

Yoshimitsu Hashimoto, Akiomi Takada, Hiroshi Takikawa, Keisuke Suzuki
A facile access has been developed to highly functionalized polycyclic isoxazoles, suitable intermediates for the synthesis of semi-aromatized polyketides, via a two-step protocol including regioselective 1,3-dipolar cycloaddition and MnO₂-mediated dehydrogenation.
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Palladium-catalyzed synthesis of 2-amino ketones from propargylic carbonates and secondary amines

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25670C, Communication

Sandro Cacchi, Giancarlo Fabrizi, Eleonora Filisti, Antonella Goggiamani, Antonia Iazzetti, Loredana Maurone
A palladium-catalyzed synthesis of 2-amino ketones from arylpropargylic carbonates and cyclic secondary amines has been developed.
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Design of a ratiometric fluorescent probe for benzenethiols based on a thiol-sulfoxide reaction

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25633A, Communication

Xuzhe Wang, Jian Cao, Chunchang Zhao
A novel thiol-sulfoxide reaction based ratiometric probe for benzenethiols was synthesized and evaluated. The probe features a chemospecific reduction over a pH range of 1-10 by benzenethiols with a marked emission color change, enabling the highly selective detection and is promising for applications.
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Helical self-assembly and co-assembly of fluorinated, preorganized discotics

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25385B, Paper

Michel H. C. J. van Houtem, Faysal Benaskar, Carel F. C. Fitie, Rafael Martin-Rapun, Jef A. J. M. Vekemans, E. W. Meijer
Fluorinated bipyridine discotics self-assemble into stable helical columnar mesophases and alternating helical assemblies with hydrocarbon bipyridine discotics in fluorinated media.
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Peripherally ethynylated carbazole-based core-modified porphyrins

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25645B, Communication

Chihiro Maeda, Naoki Yoshioka
Peripherally ethynylated carbazole-based core-modified porphyrins were synthesized by sequential metal-catalyzed coupling and annulation reactions.
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The Rabe amination after a century: direct addition of N-heterocycles to carbonyl compounds

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25595B, Communication

Daniele M. Scarpino Schietroma, Mattia R. Monaco, Valerio Bucalossi, Philipp E. Walter, Patrizia Gentili, Marco Bella
Revisiting the Rabe Amination, by means of organocatalysis, gives access to several [small alpha]-aminated aldehydes and ketones.
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Synthesis of anti and syn hydroxy-iso-evoninic acids

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25625H, Communication

Sarah A. Warren, Stephen Stokes, Christopher S. Frampton, Andrew J. P. White, Alan C. Spivey
The first synthesis of anti and syn hydroxy-iso-evoninic acid (2), a pyridyl diacid found as a macrodilactone bridging ligand in bioactive Celastraceae sesquiterpenoid-based natural products, has been achieved in 9 steps and an overall yield of 26%.
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PTSA-catalyzed Mannich-type-cyclization-oxidation tandem reactions: one-pot synthesis of 1,3,5-substituted pyrazoles from aldehydes, hydrazines and alkynes

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25487E, Communication

Pei Liu, Ying-Ming Pan, Yan-Li Xu, Heng-Shan Wang
A convenient one-pot Mannich-type-cyclization-oxidation tandem process has been developed for the synthesis of 1,3,5-trisubstituted pyrazoles derivatives from aldehydes, hydrazines and alkynes using p-toluenesulfonic acid monohydrate (PTSA) as a multifunctional catalyst.
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Solid-phase synthesis and acidolytic degradation of sterically congested oligoether dendrons

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25691F, Paper

Jeny Karabline, Moshe Portnoy
Dendronization of a solid support using a new sterically congested monomer is described. The dendrons can be disassembled back to building blocks upon acidolytic cleavage from the support.
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Porphyrin-based multi-signal chemosensors for Pb2+ and Cu2+

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25313E, Paper

Yuting Chen, Jianzhuang Jiang
Two N,N-bis(2-pyridylmethyl)amino-modified metal-free tetra(aryl)porphyrin derivatives were designed, synthesized, and characterized for application as versatile sensors for Pb²⁺ and Cu²⁺.
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Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25472G, Paper

Andrei V. Malkov, Angus J. P. Stewart-Liddon, Grant D. McGeoch, Pedro Ramirez-Lopez, Pavel Kocovsky
A series of pyridyl-oxazoline catalysts for the enantioselective reduction of both ketones and ketimines has been developed.
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Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of [small alpha]-branched aldehydes to [small beta]-nitroacrylates

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25413A, Paper

Masanori Yoshida, Erika Masaki, Hiroto Ikehara, Shoji Hara
Michael addition reaction of [small alpha]-branched aldehydes to [small beta]-nitroacrylates was successfully carried out by using a mixed catalyst consisting of a primary amino acid, L-phenylalanine, and its lithium salt to give...
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Isolation, antimicrobial activity, and absolute configuration of the furylidene tetronic acid core of pestalotic acids A-G

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25469G, Paper

Yongsheng Che
Natural products possessing the 3-(furan-2(5H)-ylidene)furan-2,4(3H,5H)-dione (furylidene tetronic acid) skeleton are rare and were encountered only as fungal metabolites. The configurational assignment of the furylidene tetronic acid core using conventional approaches...
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The origin of global and macrocyclic aromaticity in porphyrinoids

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25692D, Paper

Jun-ichi Aihara, Yuto Nakagami, Rica Sekine
Global and macrocyclic aromaticity of porphyrinoids was characterized using our graph theory of aromaticity. The sequential line plots of topological resonance energy (TRE) against the number of pi-electrons (Npi) for...
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Preferential extraction of left- or right-handed single-walled carbon nanotubes by use of chiral diporphyrin nanotweezers

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25233C, Paper

Gang Liu, Tatsuki Yasumitsu, Li Zhao, Xiaobin Peng, Feng Wang, Ajoy K. Bauri, Shuji Aonuma, Takahide Kimura, Naoki Komatsu
The 2,6-pyridylene-bridged chiral diporphyrin nanotweezers recognise handedness and diameter of SWNTs simultaneously and independently, yielding optically active SWNTs with narrow diameter range.
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A new approach to construct a fused 2-ylidene chromene ring: highly regioselective synthesis of novel chromeno quinoxalines

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25416F, Paper

K. Shiva Kumar, D. Rambabu, Bagineni Prasad, Mohammad Mujahid, G. Rama Krishna, M. V. Basaveswara Rao, C. Malla Reddy, G. R. Vanaja, Arunasree M. Kalle, Manojit Pal
Regioselective construction of a fused 2-ylidene chromene ring was achieved via a new strategy leading to novel anticancer agents.
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Continuous-flow synthesis of activated vitamin D3 and its analogues

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25511A, Paper

Shinichiro Fuse, Yuto Mifune, Nobutake Tanabe, Takashi Takahashi
A highly efficient, two-stage, continuous-flow synthesis of activated vitamin D₃ and its analogues was achieved.
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New approach to the preparation of bicyclo octane derivatives via the enantioselective cascade reaction catalyzed by chiral diamine-Ni(OAc)2 complex

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25135C, Paper

Wenyi Li, Xiaodong Liu, Zhifeng Mao, Qiao Chen, Rui Wang
Diamine-Ni(OAc)₂ complex-a highly efficient system for the preparation of chiral bicyclo octane derivatives.
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Self-assembly driven by an aromatic primary amide motif

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25117E, Perspective

Myungeun Seo, Jeyoung Park, Sang Youl Kim
This perspective highlights the key hydrogen bonding properties of primary amides determined from crystal structure studies, and a variety of supramolecular assemblies involving primary amides are discussed.
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Reactions of 1-alkyl-1,2-diphospholes with 1,3-dipoles: diphenyldiazomethane and nitrones

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25532D, Paper

Almaz Zagidullin, Yulia Ganushevich, Miluykov Vasili, Dmitry Krivolapov, Olga Kataeva, Oleg Geroldovich Sinyashin, Evamarie Hey-Hawkins
The reaction of 1-alkyl-1,2-diphosphacyclopenta-2,4-dienes (1-alkyl-1,2-diphospholes) (1) with diphenyldiazomethane proceeds at room temperature with formation of 2-alkyl-3,4,5,6,6-pentaphenyl-1,2-diphosphabicyclo[3.1.0]hex-3-enes (2). However, 1-alkyl-1,2-diphospholes (1) react with N,alpha-diphenylnitrone or N-tert-butyl-alpha-phenylnitrone depending on the temperature to...
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Radical-mediated reduction of the dithiocarbamate group under tin-free conditions

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25434D, Paper

Claire McMaster, Robert N. Bream, Richard S. Grainger
Reductive desulfurisation of dithiocarbamates is conveniently achieved using H₃PO₂-Et₃N-ACCN in refluxing dioxane.
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Synthesis of Conformationally Constrained Benzoylureas as BH3-Mimetics

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25618E, Paper

Guillaume Lessene, Ryan Michael Brady, Jonathan Bayldon Baell, IP Street, Effie Hatzis, Theresa Connor
The design of small molecules that mimic the BH3 domain and bind to Bcl-2 proteins has emerged as a promising approach to discovering novel anti-cancer therapeutics. We reveal the design...
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First total synthesis of (+)-indicanone

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25500F, Paper

Yujiro Hayashi, Kumiko Ogawa, Fuyuhiko Inagaki, Chisato Mukai
First total synthesis of (+)-indicanone based on rhodium(I)-catalyzed Pauson-Khand-type reaction of allenyne and confirmation of the complete structure were accomplished.
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Synthesis and antibacterial activity of novel neamine derivatives: preponderant role of the substituent position on the neamine core

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB07065K, Paper

Nicolas Gernigon, Valerie Bordeau, Fabienne Berree, Brice Felden, Bertrand Carboni
A series of neamine derivatives were prepared from the cyclic carbonate and sulfate of 1,3,2[prime or minute],6[prime or minute]-tetraazido-3[prime or minute],4[prime or minute],-di-O-acetylneamine.
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Asymmetric Friedel-Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25360G, Paper

Yang Jia, Wen Yang, Da-Ming Du
An efficient diastereo- and enantioselective Friedel-Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline)-Zn(OTf)₂ afforded medicinally privileged indolyl(nitro)chromans in good yields with high enantioselectivities (up to 95% ee) and diastereoselectivities under mild reaction conditions.
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Enantioselective Friedel-Crafts alkylation of indoles with 2-enoylpyridine-N-oxides catalyzed by glucoBOX-Cu(II) complex

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25315A, Paper

Jimil George, B. V. Subba Reddy
A catalytic enantioselective Friedel-Crafts reaction of indoles with 2-enoylpyridine N-oxides is reported using 5 mol% Cu(OTf)₂-glucoBOX complex.
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Facial selectivity induced by N-aryl atropisomerism in benzonitrile oxide cycloadditions with 4-methylene-2-oxazolidinones

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25271F, Paper

Sarah L. Harding, G. Paul Savage
Facial steric hindrance, by atropisomerism around the N-aryl bond, induces selectivity in nitrile oxide 1,3-dipolar cycloadditions.
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A New Ratiometric and Colorimetric Chemosensor for Cyanide Anion based on Coumarin-hemicyanine Hybrid

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25516B, Paper

Zhipeng Liu, Zhenghao Yang, Yuncong Chen, Xiaoqing Wang, Weijiang He, Yi Lu
A new ratiometric and colormetric cyanide sensor (Cou-BT) based on the nucleophilic addition of cyanide anion to the benzothiolium group of a hybrid coumarin-hemicyanine dye has been developed. Cou-BT shows...
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Synthesis of Anti-HIV Lithospermic Acid by Two Diverse Strategies

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25575H, Paper

Jih Hwu
An efficient and convergent route for the synthesis of the natural product (+)-lithospermic acid was accomplished, which possesses anti-HIV activity. The (+/-)-trans-dihydrobenzo[b]furan core therein was prepared in two different strategies....
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Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25443C, Paper

Magnus Rueping, Estibaliz Merino, Michael Bolte
A highly efficient one-pot synthesis of valuable 3,4-substituted chromenone derivatives by the reaction of 1,3-diketones with aldehydes in the presence of L-proline was developed. Chiral 3-substituted chromenones are obtained with high enantioselectivities when a chiral diarylprolinol TMS-ether is applied in the reaction.
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[2]Pseudorotaxanes, [2]rotaxanes and metal-organic rotaxane frameworks containing tetra-substituted dibenzo[24]crown-8 wheels

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25200G, Paper

Darren J. Mercer, Joe Yacoub, Kelong Zhu, Stephanie K. Loeb, Stephen J. Loeb
[2]Pseudorotaxanes, [2]rotaxanes and metal-organic rotaxane framework materials are prepared that utilise symmetrical DB24C8 analogues containing four CH₂OR (R = CH₂CH₂CH₃, CH₂(C₆H₅), C₆H₅ and C₆H₄(4-COOEt)) substituents on the 4 and 5 positions of the aromatic rings.
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Porphyrin dyads linked by a rotatable 3,3[prime or minute]-biphenyl scaffold: a new binding motif for small ditopic molecules

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25147G, Paper

Amy R. Mulholland, Pall Thordarson, Emily J. Mensforth, Steven J. Langford
The complexation behaviour of a new bis-porphyrin bearing a rotatable linker with diaza-ligands has been studied. Featuring a semi-flexible biphenyl linkage, these bis-porphyrin systems are capable of reversible binding to small ditopic molecules, opening up the possibility of developing a new generation of chemoswitchable systems.
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Dramatic influence of the substitution of alkylidene-5H-furan-2-ones in Diels-Alder cycloadditions with o-quinonedimethide as diene partner: en route to the CDEF polycyclic ring system of lactonamycin

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25299F, Paper

Sebastien Dubois, Fabien Rodier, Romain Blanc, Raphael Rahmani, Virginie Heran, Jerome Thibonnet, Laurent Commeiras, Jean-Luc Parrain
An efficient and rapid synthesis of the CDEF ring system of lactonamycinone is reported via a highly chemo- and diastereoselective intermolecular Diels-Alder cycloaddition.
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Strategies for the enantioselective synthesis of spirooxindoles

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25184A, Perspective

Nicolas R. Ball-Jones, Joseph J. Badillo, Annaliese K. Franz
This review features recent strategies for the enantioselective synthetic of spirocyclic oxindoles, focusing on reports from 2010 and 2011, while also highlighting pioneering examples from earlier work.
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First example of a heterobimetallic 'Pd-Sn' catalyst for direct activation of alcohol: efficient allylation, benzylation and propargylation of arenes, heteroarenes, active methylenes and allyl-Si nucleophiles

Org. Biomol. Chem., 2012, 10,4537-4542
DOI: 10.1039/C2OB25275A, Paper

Debjit Das, Sanjay Pratihar, Ujjal Kanti Roy, Dipakranjan Mal, Sujit Roy
Arenes, heteroarenes, 1,3-dicarbonyls and organosilicon nucleophiles undergo highly efficient alkylation with allylic, propargylic and benzylic alcohols in the presence of a new 'Pd-Sn' bimetallic catalyst.
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Steric desolation enhances the effective molarities of intramolecular H-bonding interactions

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25372K, Paper

Elena Chekmeneva, Christopher A. Hunter, Maria Cristina Misuraca, Simon M. Turega
Effective molarities for intramolecular phosphonate diester-phenol H-bonds vary with solvent indicating that changes in the solvation shell can make a significant contribution to the stability of a supramolecular complex.
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First diastereoselective synthesis of methyl caffeoyl- and feruloyl-muco-quinates

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25124H, Paper

Nikolai Kuhnert, Rakesh Jaiswal, Michael H Dickman
We report on a diastereoselective synthesis of six derivatives of caffeoyl- and feruloyl-muco-quinic acids. All the muco-quinic acid derivatives were obtained in excellent yield in five steps starting from quinic...
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Synthesis and applications of masked oxo-sulfinamides in asymmetric synthesis

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25345C, Perspective

Ramakrishna Edupuganti, Franklin A. Davis
Masked oxo-sulfinamides, protected amino carbonyl compounds, are valuable chiral building blocks for the asymmetric synthesis of functionalized nitrogen heterocycles.
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Conotoxin engineering: dual pharmacophoric noradrenaline transport inhibitor/integrin binding peptide with improved stability

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25133G, Communication

Zoltan Dekan, Ching-I Anderson Wang, Robert K. Andrews, Richard J. Lewis, Paul F. Alewood
The synthesis, biological activity and pharmacokinetics of a stable cyclic conotoxin with two independent pharmacophores are described.
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Synthesis of diversely 1,3,5-trisubstituted pyrazoles via 5-exo-dig cyclization

Org. Biomol. Chem., 2012, 10,4505-4508
DOI: 10.1039/C2OB25580D, Communication

Dmitry A. Borkin, Mirela Puscau, Alena Carlson, Agnes Solan, Kraig A. Wheeler, Bela Torok, Roman Dembinski
Tandem condensation/5-exo-dig cyclization reactions of propargyl ketone with hydrazines gives easy access to 1,3,5-unsymetrically substituted pyrazoles.
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Tandem One-Pot Synthesis of Flavans by Recyclable Silica-HClO4 catalyzed Knoevenagel Condensation and [4+2]-Diels-Alder Cycloaddition

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25376C, Paper

Sandip Bibishan Bharate, Ramesh Mudududdla, Jaideep B Bharate, Narsaiah Battini, Satyanarayana Battula, Rammohan R Yadav, Baldev Singh, Ram Vishwakarma
An efficient one-pot multi-component synthesis of flavans using perchloric acid supported on silica as a recyclable heterogeneous catalyst has been described. This is the first report of direct one-step construction...
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Synthetic Approaches to a Chiral 4-Amino-3-hydroxy Piperidine with Pharmaceutical Relevance

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25411E, Paper

Adrian Ortiz, Ian Young, David A Conlon, James Sawyer, Yi Hsiao, Amarjit Singh, Zhongping Shi
Four synthetic strategies were evaluated towards the preparation of (-)-(3R,4R)-1-benzyl-4-(benzylamino)piperidin-3-ol (1), which construct with control over the relative and absolute stereochemistry of the 4,3-amino alcohol moiety. The first strategy employed...
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Methylthioxylose - a jewel in the mycobacterial crown?

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25630D, Perspective

W. Bruce Turnbull, Susanne A. Stalford
The discovery of methylthioxylose and studies toward understanding its origins and biological roles.
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Site-specific crosslinking of annexin proteins by 1,4-benzoquinone: a novel crosslinker for the formation of protein dimers and diverse protein conjugates

Org. Biomol. Chem., 2012, 10,4500-4504
DOI: 10.1039/C2OB25460C, Communication

Peng Yu, Ivona Strug, Tanya R. Cafarella, Barbara A. Seaton, Allen Krantz
Thiol-specific crosslinking of annexin proteins using 1,4-quinone-based methodology for the coupling of proteins, and novel, diverse conjugate chemistry are described.
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Conformational flexibility of the pentasaccharide LNF-2 deduced from NMR spectroscopy and molecular dynamics simulations

Org. Biomol. Chem., 2012, 10,4577-4585
DOI: 10.1039/C2OB25189B, Paper

Elin Sawen, Florian Hinterholzinger, Clas Landersjo, Goran Widmalm
The bioactive LNF-2 pentasaccharide, with its Lewis A epitope, may have a prearranged three-dimensional structure for binding to protein receptors.
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Desymmetrizing reductive aldol cyclizations of enethioate derivatives of 1,3-diones catalyzed by a chiral copper hydride

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25206F, Paper

Jun Ou, Wing-Tak Wong, Pauline Chiu
Enethioate derivatives of prochiral 1,3-diones underwent desymmetrizing catalytic reductive aldol cyclizations to furnish [small beta]-hydroxythioesters with >98 : 2 dr, up to 94% yield and 98% ee.
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Metallic organophosphates as catalysts in asymmetric synthesis: a return journey

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25479D, Perspective

Alejandro Parra, Silvia Reboredo, Ana M. Martin Castro, Jose Aleman
This perspective provides a general overview of the most relevant topics on the applications of chiral metallic organophosphates.
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Blue-light-emitting multifunctional triphenylamine-centered starburst quinolines: synthesis, electrochemical and photophysical properties

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25120E, Paper

Peng Jiang, Dong-Dong Zhao, Xiao-Li Yang, Xiao-Lin Zhu, Jin Chang, Hong-Jun Zhu
A series of triphenylamine-centered starburst quinolines (1a-1g) have been synthesized by Friedlander condensation of the 4,4[prime or minute],4[prime or minute][prime or minute]-triacetyltriphenylamine (2) and 2-aminophenyl ketones (3a-3g) in the presence of catalytic sulfuric acid and characterized well.
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A one-pot sequence for the efficient synthesis of highly functionalized macrocarbocycles or bridged 2,8-dioxabicyclo[3.2.1]octanes from 1-nitrobicyclic compounds

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25274K, Paper

Giorgio Giorgi, Pilar Lopez-Alvarado, J. Carlos Menendez
The reaction of 1-nitrobicyclo[n.3.1]alkane-(6+n)ones with sodium borohydride followed by acidic workup led to ring opening via a one-pot sequence comprising the retro-Dieckmann-type opening of the [small alpha]-nitroketone structural fragment, followed by...
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Synthesis of selective inhibitors against V. cholerae sialidase and human cytosolic sialidase NEU2

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25335F, Paper

Zahra Khedri, Yanhong Li, Hongzhi Cao, Jingyao Qu, Hai Yu, Musleh M. Muthana, Xi Chen
Sialidases or neuraminidases catalyze the hydrolysis of terminal sialic acid residues from sialyl oligosaccharides and glycoconjugates. Despite successes in developing potent inhibitors specifically against influenza virus neuraminidases, the progress in...
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Highly enantioselective Biginelli reaction catalyzed by SPINOL-phosphoric acids

Org. Biomol. Chem., 2012, 10,4467-4470
DOI: 10.1039/C2OB25663K, Paper

Fangxi Xu, Dan Huang, Xufeng Lin, Yanguang Wang
A highly enantioselective Biginelli reaction promoted by chiral spirocyclic SPINOL-phosphoric acids has been developed. Under the optimized conditions a wide range of optically active dihydropyrimidinethiones were obtained in high yields with good to excellent enantioselectivities. The synthetic utility of this method was demonstrated by the synthesis of chiral precursors of three drugs, including (S)-Monastrol, (S)-L-771688 and (S)-SQ 32926.
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Antituberculosis agent diaportheone B: Synthesis, absolute configuration assignment, and anti-TB activity of its analogues

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25831E, Paper

Pandrangi Siva Swaroop, Gajanan N Raut, Rajesh Gonnade, Priyanaka Verma, Rajesh Gokhale, D SRINIVASA REDDY
First synthesis of diaportheone B, an antituberculosis agent isolated from endophytic fungus Diaporthe sp. P133 is reported in two complementary routes, one step and three-step sequence. The absolute configuration of...
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Hypervalent iodine mediated synthesis of carbamate protected p-quinone monoimine ketals and p-benzoquinone monoketals

Org. Biomol. Chem., 2012, 10,4549-4553
DOI: 10.1039/C2OB25089F, Paper

Naganjaneyulu Bodipati, Rama Krishna Peddinti
A practical synthesis of p-quinone monoimide ketals and p-quinone monoketals are obtained from single starting materials, viz. 4-methoxyanilides, under different conditions. The double oxidation on simple anilides provided p-quinone monoimide ketals.
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Synthesis of amino-substituted indoles using the Bartoli reaction

Org. Biomol. Chem., 2012, 10,4441-4447
DOI: 10.1039/C2OB25256B, Paper

Laura Wylie, Paolo Innocenti, Daniel K. Whelligan, Swen Hoelder
We report herein the concise preparation of a range of functionalised aminoindoles via a new application of the Bartoli reaction.
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Rubesanolides C-E: abietane diterpenoids isolated from Isodon rubescens and evaluation of their anti-biofilm activity

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25192B, Paper

Juan Zou, Lutai Pan, Qiji Li, Jianxin Pu, Ping Yao, Min Zhu, Jeffrey A. Banas, Hongjie Zhang, Handong Sun
Rubesanolides C-E (1-3), abietane diterpenes containing a unique [gamma]-lactone subgroup between C-8 and C-20, were identified from Isodon rubescens.
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A smooth rearrangement of N-p-toluenesulfonyl 2-tert-butyldiphenylsilylmethyl-substituted azetidines into N-p-toluenesulfonyl 3-tert-butyldiphenylsilyl-substituted pyrrolidines

Org. Biomol. Chem., 2012, 10,4390-4399
DOI: 10.1039/C2OB07140A, Paper

Bharat D. Narhe, Vardhineedi Sriramurthy, Veejendra K. Yadav
On exposure to BF₃[middle dot]OEt₂, the azetidine [rightward arrow] pyrrolidine transformation proceeds through a non-concerted [sigma]_C-N cleavage, siliranium ion formation and an intramolecular S_N2 reaction.
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Computational studies on the mechanism of the gold(I)-catalysed rearrangement of cyclopropenes

Org. Biomol. Chem., 2012, 10,4433-4440
DOI: 10.1039/C2OB25183C, Paper

Maximillian S. Hadfield, L. Jonas L. Haller, Ai-Lan Lee, Stuart A. Macgregor, James A. T. O'Neill, Ashley M. Watson
Density functional theory calculations have been employed to investigate the mechanism of gold(I)-catalysed rearrangements of cyclopropenes.
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The Role of Cyclobutenes in Gold(I)-Catalysed Skeletal Rearrangement of 1,6-Enynes

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25419K, Paper

Antonio M. Echavarren, Ana Escribano-Cuesta, Patricia Perez-Galan, Elena Herrero-Gomez, Masaki Sekine, Ataualpa A. C. Braga, Feliu Maseras
1,6-Enynes with electron-donating substituents at the alkyne undergo gold(I)-catalysed single cleavage skeletal rearrangement, whereas substrates with electron-withdrawing substituents evolve selectively to double cleavage rearrangement. Theoretical calculations provide a qualitative rationale...
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Organocatalytic dendrimers

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25317H, Perspective

Brian Rasmussen, Jorn Bolstad Christensen
The combination of dendritic catalysis and organocatalysis.
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Kinetics and mechanism of the racemic addition of trimethylsilyl cyanide to aldehydes catalysed by Lewis bases

Org. Biomol. Chem., 2012, 10,4289-4298
DOI: 10.1039/C2OB25188D, Paper

Michael North, Marta Omedes-Pujol, Carl Young
The addition of trimethylsilyl cyanide to aldehydes is shown to be subject to Lewis and/or Bronsted base catalysis.
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VCD to determine absolute configuration of natural product molecules: secolignans from Peperomia blanda

Org. Biomol. Chem., 2012, 10,4208-4214
DOI: 10.1039/C2OB25109D, Paper

Lidiane G. Felippe, Joao M. Batista Jr., Debora C. Baldoqui, Isabele R. Nascimento, Massuo J. Kato, Yanan He, Laurence A. Nafie, Maysa Furlan
The absolute configuration of a new secolignan from Peperomia blanda (Piperaceae) was determined using VCD and DFT calculations.
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