Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Multi-channel colorimetric and fluorescent probes for differentiating between cysteine and glutathione/homocysteine

16 October, 2014 - 08:17

Org. Biomol. Chem., 2014, 12,8422-8427
DOI: 10.1039/C4OB01219D, PaperLun Song, Ti Jia, Wenjia Lu, Nengqin Jia, Weibing Zhang, Junhong Qian
Three fluorescent probes were rationally designed to discriminate between Cys and GSH/Hcy. Cys and GSH can be differentiated by the naked eye.
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Two-channel dansyl/tryptophan emitters with a cholic acid bridge as reporters for local hydrophobicity within supramolecular systems based on bile salts

16 October, 2014 - 08:17

Org. Biomol. Chem., 2014, 12,8499-8504
DOI: 10.1039/C4OB01394H, PaperM. Gomez-Mendoza, M. Luisa Marin, Miguel A. Miranda
Simultaneous emission from the Trp and Dns fluorophores of linked dyads in biomimetic media is quenched by iodide anions with rate constants that depend on the local hydrophobicity.
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ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels-Alder reactions: synthesis of dihydropyran-fused diterpenoids

16 October, 2014 - 08:17

Org. Biomol. Chem., 2014, 12,8442-8452
DOI: 10.1039/C4OB01040J, PaperChunyong Ding, Lili Wang, Haijun Chen, Christopher Wild, Na Ye, Ye Ding, Tianzhi Wang, Mark A. White, Qiang Shen, Jia Zhou
A mild and concise approach for the construction of a 3,4-dihydro-2H-pyran ring integrated into the A-ring of the natural product oridonin is reported herein.
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A general Pd/Cu-catalyzed C-H heteroarylation of 3-bromoquinolin-2(1H)-ones

16 October, 2014 - 08:17

Org. Biomol. Chem., 2014, 12,8533-8541
DOI: 10.1039/C4OB01610F, PaperAlexandre Bruneau, Jean-Daniel Brion, Samir Messaoudi, Mouad Alami
The Pd(OAc)2/CuI system effectively catalyzes the coupling of 3-bromoquinolin-2(1H)-ones with a series of azoles to give 3-(heteroaryl)quinolin-2(1H)-ones in good yields.
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The mechanism and regioselectivity of gold(I) or platinum(II) catalyzed intramolecular hydroarylation to pyrrolopyridinones and pyrroloazepinones

16 October, 2014 - 08:17

Org. Biomol. Chem., 2014, 12,8433-8441
DOI: 10.1039/C4OB00894D, PaperRan Fang, Xiaoxiao Wei, Lizi Yang
Pyrrolopyridinones and pyrroloazepinones can be prepared through gold(I) or platinum(II) catalysis. These interesting gold(I) or platinum(II) catalyses are fully supported by a computational study justifying the formation of each intermediate.
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Direct synthesis of polysubstituted 2-aminothiophenes by Cu(II)-catalyzed addition/oxidative cyclization of alkynoates with thioamides

16 October, 2014 - 08:17

Org. Biomol. Chem., 2014, 12,8473-8479
DOI: 10.1039/C4OB01534G, PaperLi-Shi Ge, Zheng-Lin Wang, Xing-Lan An, Xiaoyan Luo, Wei-Ping Deng
Cu(II)-catalyzed addition/oxidative cyclization of thioamides with alkynoates affords structurally important 2-aminothiophenes in moderate to excellent yields.
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Facile synthesis of antimalarial 1,2-disubstituted 4-quinolones from 1,3-bisaryl-monothio-1,3-diketones

16 October, 2014 - 08:17

Org. Biomol. Chem., 2014, 12,8555-8561
DOI: 10.1039/C4OB01455C, PaperAjjampura C. Vinayaka, Maralinganadoddi P. Sadashiva, Xianzhu Wu, Sergei S. Biryukov, Jose A. Stoute, Kanchugarakoppal S. Rangappa, D. Channe Gowda
A novel strategy is developed to access excellent antimalarial 1,2-disubstituted 4-quinolones in high yield starting from 1,3-bisaryl-monothio-1,3-diketone using Pd(OAc)2 as a catalyst without any ligand requirement.
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Oxyma-B, an excellent racemization suppressor for peptide synthesis

16 October, 2014 - 08:17

Org. Biomol. Chem., 2014, 12,8379-8385
DOI: 10.1039/C4OB01612B, CommunicationYahya E. Jad, Sherine N. Khattab, Beatriz G. de la Torre, Thavendran Govender, Hendrik G. Kruger, Ayman El-Faham, Fernando Albericio
Oxyma-B, a superb additive for the control of optical purity during the synthesis of peptides.
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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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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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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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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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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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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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Radical Reactions of Borohydrides

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01784F, Review ArticleTakuji Kawamoto, Ilhyong Ryu
Borohydrides are an important class of reagents in both organic and inorganic chemistry. Though popular as hydride-transfer reagents for reduction, since earlier work from the 1970s, borohydride reagents have also...
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Fischer indolisation of N-([small alpha]-ketoacyl)anthranilic acids into 2-(indol-2-carboxamido)benzoic acids and 2-indolyl-3,1-benzoxazin-4-ones and their NMR study

14 October, 2014 - 07:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01714E, PaperKarel Proisl, Stanislav Kafka, Damijana Urankar, Martin Gazvoda, Roman Kimmel, Janez Kosmrlj
N-([small alpha]-ketoacyl)anthranilic acids reacted with phenylhydrazinium chloride in boiling acetic acid to afford 2-(indol-2-carboxamido)benzoic acids in good to excellent yields and 2-indolyl-3,1-benzoxazin-4-ones as by-products. The formation of the latter products could...
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