Royal Society of Chemistry

Linear versus Branched poly-Lysine/Arginine as Polarity Enhancer Tags

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01354A, CommunicationFernando Albericio, Marta Paradis-Bas, Maria Albert-Soriano, Judit Tulla-Puche
The design and synthesis of Lys- and Arg-containing peptide as solubilizing tags were studied to evaluate their influence on polarity. The relevance of spatial arrangement of polar groups, in [small alpha]-...
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Linear synthesis of the branched pentasaccharide repeats of O-antigens from Shigella flexneri 1a and 1b demonstrating major steric hindrance associated to type-specific glucosylation

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01200C, PaperJason Hargreaves, Yann Le Guen, Catherine Guerreiro, Karine Descroix, Laurence A. MULARD
Shigella flexneri serotypes 1b and 1a are Gram-negative enteroinvasive bacteria causing shigellosis in humans. The O-antigen from S. flexneri 1b is a {[rightward arrow]2)-[3Ac/4Ac]-[small alpha]-L-Rhap-(1[rightward arrow]2)-[small alpha]-L-Rhap-(1[rightward arrow]3)-[2Ac]-[small alpha]-L-Rhap-(1[rightward arrow]3)-[[small alpha]-D-Glcp-(1[rightward arrow]4)]-[small beta]-D-GlcpNAc-(1[rightward arrow]}n branched polysaccharide ({AcABAcC(E)D}n). It is identical to...
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Synthesis of Aromatic 13C/2H-alpha-Ketoacid Precursors to be Used in Selective Phenylalanine and Tyrosine Protein Labelling

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01129E, PaperRoman Josef Lichtenecker
The application of labelled [small alpha]-ketoacids as additives in cell-based protein expression systems is a routinely used tool for introducing stable isotopes at distinct positions of aliphatic residues in the target...
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Nickel-Catalyzed Substitution Reactions of Propargyl Halides with Organotitanium Reagents

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00677A, Review ArticleQinghan Li, Jung-Wei Liao, Yi-Ling Huang, Ruei-Tang Chiang, Han-Mou Gau
A simple and mild catalytic coupling reaction of propargyl halides with organotitanium reagents is reported. The reaction of propargyl bromide with organo-titanium reagents mediated by NiCl2 and PCy3 in CH2Cl2...
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A Neighboring Group Participation Strategy: Direct and Highly Diastereoselective Synthesis of 2-Substituted and 2,2-Bisubstituted Perhydrofuro[2,3-b]pyran Derivatives

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00642A, PaperHuawu Shao, Xiaofeng Ma, Qin Tang, Jun Ke, Jichao Zhang, Xinglong Yang, Xudong Shen
Treatment of methyl 2-C-formylmethyl-2-deoxy-[small beta]-D-glucopyranoside (5) or methyl 2-C-acetylmethyl-2-deoxy-[small beta]-D-glucopyranoside (1) with H2SO4-HOAc-Ac2O gave 2-acetoxyl-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]hexahydrofuro[2,3-b]pyran (6) and acetyl 2-C-acetylmethyl-2-deoxy-[small alpha]-D-glucopyranoside (7) respectively, which were further reacted with nucleophiles in the presence of TMSOTf...
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Novel Ruthenium-Catalyst for Hydroesterification of Olefins with Formates

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01246A, CommunicationIvana Fleischer, Irina Profir, Matthias Beller
An alternative ruthenium-based catalyst for the hydroesterification of olefins with formates is reported. The good activity of our system is ensured by the use of a bidentate P,N-ligand and ruthenium...
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Synthesis of a chiral building block for highly functionalized polycyclic ethers

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01439A, PaperYagamare Fall, Gonzalo Pazos, Manuel Perez, Zoila Gandara, Generosa Gomez
An efficient procedure for preparing enantiopure polycyclic ethers is reported. The protocol is based in the photo-oxidation/conjugate addition sequence over a chiral functionalized furan, which was prepared from commercially available...
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Silver Triflate and Triflic Anhydride-Promoted Expedient Synthesis of Acylated 1-Aminoisoquinolines

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01301H, CommunicationYuewen Li, Liang Gao, Hui Zhu, Guangming Li, Zhiyuan Chen
A practical and convergent synthesis of biologically active 1-(N-acyl)-1-aminoisoquinolines from the reaction of 2-alkynylbenzaldoximes with amides has been realized. The readily available amides could be activated by triflic anhydride (Tf2O)...
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A Facile Manganese Dioxide Mediated Oxidation of Primary Benzylamines to Benzamides

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01166J, PaperAnna Poeschl, David M Mountford
A high yielding manganese dioxide mediated oxidation of benzylamines to the corresponding amides has been developed under mild reaction conditions. The mechanism for the conversion has been explored by 1H...
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A versatile strategy for appending a single functional group to a multifunctional host through host-guest covalent-capture

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01429D, PaperJean-noel Rebilly, Benoit Colasson, Olivia Reinaud, Assia Hessani
Mono-functionalization of a molecular host is a key step for the development of various efficient systems ranging from supramolecular fluorescent probes to supramolecular catalysts. The presence of several identical reactive...
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Approaches to the total synthesis of chaetochalasin A

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01308E, PaperE J Thomas, Mark Willis
Chaetochalasin A is a complex natural product whose biosynthesis may involve two domino Diels Alder reactions. Approaches to the total synthesis of chaetochalasin A using this approach have been studied....
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Cooperative Hybridization of [gamma]PNA Miniprobes to a Repeating Sequence Motif and Application to Telomere Analysis

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00953C, PaperHa H. Pham, Connor T. Murphy, Gopalsamy Sureshkumar, Danith H Ly, Patricia L. Opresko, Bruce Armitage
GammaPNA oligomers having one or two repeats of the sequence AATCCC were designed to hybridize to DNA having one or more repeats of the complementary TTAGGG sequence found in the...
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First total synthesis of antihypertensive natural products S-(+)-XJP and R-(-)-XJP

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01470G, PaperChaoLei Wang, Guoxiang Wei, Xue Yang, Hequan Yao, Jieyun Jiang, Jie Liu, Mingqin Shen, Xiaoming Wu, Jinyi Xu
The first asymmetric total synthesis of antihypertensive natural products S-(+)-XJP and R-(-)-XJP have been achieved in 8 steps starting from commercially available 6-bromo-2-hydroxy-3-methoxybenzaldehyde 6. Key steps include intramolecular Heck reaction...
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Synthesis of tumor-associated MUC1-glycopeptides and their multivalent presentation by functionalized gold colloids

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01339E, PaperIsabella Tavernaro, Sebastian Hartmann, Laura Sommer, Heike Hausmann, Christian Rohner, Martin Ruehl, Anja Hoffmann-Roder, Sabine Schlecht
The mucin MUC1 is a glycoprotein involved in fundamental biological processes, which can be found over-expressed and with a distinctly altered glycan pattern on epithelial tumor cells, thus it is...
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Total Synthesis of Macrodiolide Ionophores Aplasmomycin and Boromycin via Double Ring Contraction

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01017E, PaperJames D White, Mitchell A Avery, Brian Gray, Alan Whittle, Prakash Dhingra, Shen-chun Kuo, Satish C Choudhry, Myung-chol Kang, Thalatani R. Vedananda
The half structure of the symmetrical macrodiolide aplasmomycin A was synthesized by alkylation of a C3-C10 -sulfonyl ketone subunit, prepared from (R)-pulegone and protected as a C3 ortholactone with (2R,3R)-butanediol,...
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Developing principles for predicting ionic liquid effects on reaction outcome. A demonstration using a simple condensation reaction

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01070A, PaperSinead T Keaveney, Karin S Schaffarczyk McHale, Ronald S Haines, Jason B Harper
The effects of a series of ionic liquids, with systematic variations in the cation, on the condensation of an alkyl amine with an aromatic aldehyde were investigated, and the outcomes...
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Indole synthesis from N-allenyl-2-iodoanilines under mild conditions mediated by samarium(II) diiodide

Org. and Biomol. Chem. - 31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01164C, CommunicationHiroki Iwasaki, Kenji Suzuki, Mitsunari Yamane, Shohei Yoshida, Naoto Kojima, Minoru Ozeki, Masayuki Yamashita
A novel method for indole skeleton synthesis under mild conditions mediated by samarium(II) diiodide has been developed.
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A convenient tandem one-pot synthesis of donor-acceptor-type triphenylene 2,3-dicarboxylic esters from diarylacetylene

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01503G, Communicationchun Feng, Xian-Li Tian, Jing Zhou, Shi-Kai Xiang, Wen-Hao Yu, Bi-Qin Wang, Ping Hu, Carl Redshaw, Keqing Zhao
A tandem one-pot method for the direct synthesis of polysubstituted triphenylene 2,3-dicarboxylic esters with different substitution patterns has been developed through enyne metathesis of diarylacetylene, followed by Diels-Alder, aromatization and...
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68Ga based Probe for Alzheimer's Disease: Synthesis and Preclinical Evaluation of Homodimeric Chalcone in [small beta]-Amyloid Imaging

Org. and Biomol. Chem. - 31 July, 2014 - 11:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00941J, PaperKanchan Chauhan, Anupama Datta, Anupriya Adhikari, Krishna Chuttani, Ajai kumar Singh, Anil K Mishra
In an attempt to explore PET radioisotope, 68Ga in the diagnosis of Alzheimer's disease, a metal based homodimeric ligand exhibiting high affinity towards A[small beta] aggregates was designed by conjugating two...
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Short asymmetric synthesis of phenanthroindolizidines through chiral homoallylic sulfinamines

Org. and Biomol. Chem. - 31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01133C, PaperCintia Anton-Torrecillas, Jose C. Gonzalez-Gomez
An expeditious synthesis of enantioenriched phenanthroindolizidines has been achieved using tert-butylsulfinamide as a chiral inductor and without any other protecting group.
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