Org. and Biomol. Chem.

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Direct C-H bond arylation of fluorenes with aryl chlorides catalyzed by N-heterocyclic carbene-palladium(II)-1-methylimidazole complex and further transformation of the products in a one-pot procedure

16 October, 2014 - 08:17

Org. Biomol. Chem., 2014, 12,8488-8498
DOI: 10.1039/C4OB01594K, PaperYa-Yun Ji, Li-Li Lu, Yu-Chun Shi, Li-Xiong Shao
Direct C-H arylation of fluorenes with aryl chlorides and transformation of the products in a one-pot procedure was reported.
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Concise synthesis of 2,4-disubstituted thiazoles from [small beta]-azido disulfides and carboxylic acids or anhydrides: asymmetric synthesis of cystothiazole C

16 October, 2014 - 08:17

Org. Biomol. Chem., 2014, 12,8453-8461
DOI: 10.1039/C4OB01460J, PaperYi Liu, Xue Sun, Xing Zhang, Jun Liu, Yuguo Du
A novel and efficient method for one-pot synthesis of 2,4-disubstituted thiazoles from carboxylic acids or anhydrides is established. Based on this new methodology, the total synthesis of the bis-2,4-disubstituted bis(thiazoles) natural product cystothiazole C is also presented.
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HBTU mediated 1-hydroxybenzotriazole (HOBt) conjugate addition: synthesis and stereochemical analysis of [small beta]-benzotriazole N-oxide substituted [gamma]-amino acids and hybrid peptides

16 October, 2014 - 08:17

Org. Biomol. Chem., 2014, 12,8462-8472
DOI: 10.1039/C4OB01548G, PaperSachitanand M. Mali, Mothukuri Ganesh Kumar, Mona M. Katariya, Hosahudya N. Gopi
Synthesis and conformational analysis of [small beta]-benzotriazole N-oxide ([small beta]-BtO) substituted [gamma]-amino acids by direct conjugate addition of HOBt to E-vinylogous [gamma]-amino acids are reported.
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First total synthesis of ganglioside DSG-A possessing neuritogenic activity

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01882F, CommunicationYow-Fu Tsai, Yu-Fa Wu, Jhe-Ruei Guo, Cheng-Ping Yu, Hui-Ming Yu, Chun-Chen Liao
The first total synthesis of ganglioside DSG-A (1) has been achieved via chemoselective glycosylation and a [1+1+2] synthetic strategy. We have also developed an efficient method that can be handled...
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Correction: Stereocontrolled lithiation/trapping of chiral 2-alkylideneaziridines: investigation into the role of the aziridine nitrogen stereodynamics

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB90144D, CorrectionRosmara Mansueto, Leonardo Degennaro, Jean-Francois Briere, Karen Griffin, Michael Shipman, Saverio Florio, Renzo Luisi
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Facile diverted synthesis of pyrrolidinyl triazoles using organotrifluoroborate: Discovery of potential mPTP blockers

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01967A, PaperSun hwa Jung, Kihang Choi, AN Pae, Jae Kyun Lee, H Choo, Gyochang Keum, Yong Seo Cho, Sun-Joon Min
This article describes the rapid and diverted synthesis of pyrrolidinyl triazoles for the discovery of mitochondrial permeability transition pore (mPTP) blockers. The 1,3-dipolar cycloaddition of ethynyl trifluoroborate with azidopyrrolidine produced...
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Synthesis and LC-MS/MS Analysis of Desmosine-CH2, a Potential Internal Standard for the Degraded Elastin Biomarker Desmosine

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01438C, PaperYuko Murakami, Rina Suzuki, Hiroto Yanuma, Jiangtao He, Shuren Ma, Gerard M Turino, Yong Y Lin, Toyonobu Usuki
Desmosine-CH2, an analog of the elastic tissue degradation biomarker desmosine, can be regarded as a potential internal standard for precise quantification of desmosines by LC-MS/MS. In this study, the chemical...
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Organocatalytic Michael addition-lactonisation of carboxylic acids using [small alpha],[small beta]-unsaturated trichloromethyl ketones as [small alpha],[small beta]-unsaturated ester equivalents

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01788A, PaperLouis C. Morrill, Daniel G. Stark, James E. Taylor, Siobhan R. Smith, James A. Squires, Agathe C. A. D'Hollander, Carmen Simal, Peter Shapland, Timothy J. C. O'Riordan, Andrew D. Smith
Isothiourea HBTM-2.1 catalyses the Michael addition-lactonisation of 2-aryl and 2-alkenylacetic acids and [small alpha],[small beta]-unsaturated trichloromethyl ketones.
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pKa Modulation in Rhodamine Based Probes for Colorimetric Detection of Picric Acid

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02001D, CommunicationNagarajan V, Bamaprasad Bag
Tuning of pKa in acid sensitive rhodamine spirolactam derivatives as a function of solvent medium resulted in selective detection of picric acid from its lower nitro phenolic analogues and few...
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Gold-catalyzed Carboalkoxylations of 2-Ethynylbenzyl Ethers to Form 1- and 3-Substituted 2-Methoxy-1-Hindenes: Bronsted Acid Versus Gold Catalysis

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01794C, PaperRai-Shung Liu, Chun-Hao Chen, Chiou-Dong Wang, Yi-Feng Hsieh
Selective synthesis of 1- and 3-substituted 2-methoxyindenes from the carboalkoxylations of 2-ethynylbenzyl ethers is described; the former is obtained efficiently with P(t-Bu)2(obiphenyl) AuCl/NaBARF in DCM/MS 4A whereas the latter is...
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Templated DNA ligation with thiol chemistry

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01552E, CommunicationDadong Li, Xiaojian Wang, Fubo Shi, Ruojie Sha, Nadrian C. Seeman, James W. Canary
Templated DNA ligation reactions are useful in a variety of contexts and have drawn much attention recently. Herein we describe two different DNA-templated ligation systems based on thiols and thiol-mediated chemistry. One system follows the principle of native chemical ligation reaction, and the other utilizes a thiol-disulfide exchange reaction.
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Asymmetric Synthesis of Axially Chiral Anilides by Pd-Catalyzed Allylic Substitutions with P/Olefin Ligands

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01087F, PaperYilin Liu, Xiangqing Feng, HAIFENG DU
As an attractive class of non-biaryl atropisomeric compounds, C-N axially chiral anilides have received considerable attention, and several methods have been successfully developed for their synthesis. Pd-catalyzed asymmetric allylic aminations...
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Efficient synthesis of oligosaccharyl 1,2-O-orthoesters from n-pentenyl glycosides and application to the pentaarabinofuranoside of mycobacterial cell surface

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01395F, PaperShivaji A Thadke, Srinivas Hotha
Complex oligosaccharide syntheses employ the use of more than one glycosyl donor and hence, methods for the interconversion of glycosyl donors are highly valuable for the overall synthesis plan. Herein,...
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Efficient Silver-Catalyzed Direct Sulfenylation and Selenylation of Rich Arenes

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01992J, PaperGuobing Yan, Arun Jyoti Borah, Lianggui Wang
An efficient protocol for silver/copper-cocatalyzed direct sulfenylation and selenylation of arenes with aryl disulfides and diselenides has been developed. This strategy exhibits excellent functional group tolerance and high regioselectivity. Mono...
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Comparative perspective and synthetic applications of transition metal mediated oxidative cyclisation of 1,5-dienes towards cis-2,5-disubstituted tetrahydrofurans

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01491J, Review ArticleNadeem S. Sheikh
Cis-2,5-disubstituted tetrahydrofurans constitute the core of several natural products and synthetic analogues which exhibit a broad and interesting range of biological activities. This review highlights a personal perspective and provides...
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Diastereoselective Photodimerization Reactions of Chromone-2-carboxamides to Construct a C2-Chiral Scaffold

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01827C, PaperFumitoshi Yagishita, Nozomi Baba, Yuki Ueda, Satoshi Katabira, Yoshio Kasashima, Takashi Mino, Masami Sakamoto
Irradiation of three chromone-2-carboxamides with a chiral auxiliary resulted in diastereoselective formation of a C2-chiral anti-HH dimer scaffold. Selection of the solvent polarity and decreasing the temperature resulted in asymmetric...
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Catalytic Asymmetric Povarov Reaction of Isatin-derived 2-Azadienes with 3-Vinylindoles

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01741B, PaperHong-Hao Zhang, Xiao-Xue Sun, Jing Liang, Yue-Ming Wang, Chang-Chun Zhao, Feng Shi
The first catalytic asymmetric Povarov reaction of isatin-derived 2-azadienes with 3-vinylindoles has been established in the presence of chiral phosphoric acid, which tolerates a wide range of substrates in generally...
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One Pot Synthesis of Pyrrolo[3,4-c]quinolinone/Pyrrolo[3,4-c]quinoline Derivatives from 2-Aminoarylacrylates/2-Aminochalcones and Tosylmethyl isocyanide (TosMIC)

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01580K, PaperXin-Mou Lu, Jian Li, Zhong-Jian Cai, Rong Wang, Shun-Yi Wang, Shun-Jun Ji
An efficient and practical synthetic approach to access of 2H-pyrrolo[3,4-c]quinolin-4(5H)-one/2H-pyrrolo[3,4-c]quinoline derivatives by the reaction of 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC) via one pot van Leusen reaction and cyclization under basic...
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Design and synthesis of potent hydroxamate inhibitors with increased selectivity within the gelatinase family

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01516A, PaperAna Ramos, Jose Maria Zapico, Anna Puckowska, Kamila Filipiak, Claire Coderch, Beatriz de Pascual-Teresa
MMP-2 is a validated target for the development of anticancer agents. Herein we describe the synthesis of a new series of potent phenylalanine derived hydroxamates, with increased MMP-2/MMP-9 selectivity compared...
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A short designed semi-aromatic organic nanotube - synthesis, chiroptical characterization, and host properties

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01683A, PaperTorbjorn Wixe, Niels Johan Christensen, Sven Lidin, Peter Fristrup, Kenneth Warnmark
A short helical nanotube having its aromatic system perpendicular to its axis of propagation was synthesized and its properties were studied.
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