Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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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 - 07:17

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 - 07:17

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 - 07:17

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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Stereocontrolled lithiation/trapping of chiral 2-alkylideneaziridines: investigation into the role of the aziridine nitrogen stereodynamics

14 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8505-8511
DOI: 10.1039/C4OB01457J, PaperRosmara Mansueto, Leonardo Degennaro, Jean-Francois Briere, Karen Griffin, Michael Shipman, Saverio Florio, Renzo Luisi
The origin of the stereoselectivity in the lithiation/trapping of 2-alkylideneaziridines bearing a chiral group as the nitrogen substituent was investigated.
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New ganglio-tripod amphiphiles (TPAs) for membrane protein solubilization and stabilization: implications for detergent structure-property relationships

14 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8480-8487
DOI: 10.1039/C4OB01375A, PaperPil Seok Chae, Hyoung Eun Bae, Muhammad Ehsan, Hazrat Hussain, Jin Woong Kim
This study introduces new ganglio-TPAs with enhanced efficacy for membrane protein solubilization and stabilization compared to conventional detergents.
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Cycloreversion of [small beta]-lactams via photoinduced electron transfer

14 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8428-8432
DOI: 10.1039/C4OB01416B, PaperRaul Perez-Ruiz, Jose A. Saez, M. Consuelo Jimenez, Miguel A. Miranda
With DABCO as an electron donor, photoinduced cycloreversion of [small beta]-lactams leads to olefins through 1,4-radical anions and 1,4-biradicals as intermediates.
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Mechanisms for enzymatic cleavage of the N-glycosidic bond in DNA

14 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8367-8378
DOI: 10.1039/C4OB01063A, Review ArticleAlexander C. Drohat, Atanu Maiti
We review advances in understanding the mechanism of DNA glycosylases, emphasizing the role of the nucleobase leaving-group.
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Synthesis of L-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors

14 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8415-8421
DOI: 10.1039/C4OB01319K, PaperSiddamal Reddy Putapatri, Abhinav Kanwal, Balasubramanian Sridhar, Sanjay K. Banerjee, Srinivas Kantevari
Fused chiral bicyclic 1,2,3-triazoles synthesized from commercially available natural L-rhamnose exhibited excellent SGLT inhibition activity.
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The first stereoselective total synthesis of neosemburin and isoneosemburin

14 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8408-8414
DOI: 10.1039/C4OB01239A, PaperGadi Madhusudhan Reddy, Perali Ramu Sridhar
The stereoselective total synthesis of neosemburin and isoneosemburin was achieved using 3-C-branched sugar precursors which in turn were synthesized by Claisen rearrangement of sugar derived allyl vinyl ethers.
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Triflic acid-promoted cycloisomerization of 2-alkynylphenyl isothiocyanates and isocyanates: a novel synthetic method for a variety of indole derivatives

14 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8398-8407
DOI: 10.1039/C4OB00825A, PaperTakao Saito, Yoshihiko Sonoki, Takashi Otani, Noriki Kutsumura
A unique method for synthesis of structurally diverse types of indoles involving a triflic acid-promoted cycloisomerization and a Wagner-Meerwein-type rearrangement is described.
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Synthesis and characterisation of glucosamine-NSAID bioconjugates

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8325-8335
DOI: 10.1039/C4OB01681E, PaperRachel A. Jones, Yann Thillier, Siva S. Panda, Nicole Rivera Rosario, C. Dennis Hall, Alan R. Katritzky
Synthetic strategies to prepare non-steroidal anti-inflammatory drug-glucosamine bioconjugates.
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Synthesis of enantiomerically enriched indolines and tetrahydroisoquinolines from (S)-amino acid-derived chiral carbocations: an easy access to (3S,4R)-demethoxy-3-isopropyl diclofensine

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8318-8324
DOI: 10.1039/C4OB00922C, PaperSudipta Kumar Manna, Gautam Panda
Enantiomerically enriched indolines and tetrahydroisoquinolines were synthesized in high yields from easily accessible (S)-amino acid-derived chiral carbocations.
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Peptidomimetic inhibitors of N-myristoyltransferase from human malaria and leishmaniasis parasites

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8132-8137
DOI: 10.1039/C4OB01669F, CommunicationTayo O. Olaleye, James A. Brannigan, Shirley M. Roberts, Robin J. Leatherbarrow, Anthony J. Wilkinson, Edward W. Tate
Peptidomimetic inhibitors of N-myristoyltransferase from malaria and leishmaniasis parasites have been designed with nanomolar potency, and reveal the first direct structural evidence for a ternary NMT/CoA/myristoyl peptide product complex.
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Performance of DFT methods and origin of stereoselectivity in bipyridine N,N[prime or minute]-dioxide catalyzed allylation and propargylation reactions

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8346-8353
DOI: 10.1039/C4OB01719F, PaperDiana Sepulveda, Tongxiang Lu, Steven E. Wheeler
It is shown that many DFT methods correctly predict the stereoselectivity of bipyridine N,N[prime or minute]-dioxide catalyzed alkylation reactions despite predicting the incorrect low-lying transition state structures. A novel explanation of the origin of stereoselectivity in these reactions is also provided.
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Base-promoted annulation of [small alpha]-hydroxy ketones and dimethyl but-2-ynedioate: straightforward access to pyrano[4,3-a]quinolizine-1,4,6(2H)-triones and 2H-pyran-2,5(6H)-diones

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8128-8131
DOI: 10.1039/C4OB01858C, CommunicationHaitao He, Chaorong Qi, Yanglu Ou, Wenfang Xiong, Xiaohan Hu, Yanwei Ren, Huanfeng Jiang
A novel direct synthesis of pyrano[4,3-a]quinolizine-1,4,6(2H)-triones and 2H-pyran-2,5(6H)-diones from [small alpha]-hydroxy ketones and dimethyl but-2-ynedioate via a base-promoted cascade annulation has been developed.
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Synthesis of substituted azafluorenones from dihalogeno diaryl ketones by palladium-catalyzed auto-tandem processes

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8138-8141
DOI: 10.1039/C4OB01629G, CommunicationNada Marquise, Vincent Dorcet, Floris Chevallier, Florence Mongin
Auto-tandem processes combining either Suzuki or Heck coupling with direct cyclizing arylation are described.
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Oxidative damage of aromatic dipeptides by the environmental oxidants NO2[radical dot] and O3

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8280-8287
DOI: 10.1039/C4OB01577K, PaperL. F. Gamon, J. M. White, U. Wille
Irreversible oxidative damage at both aromatic side chains and dipeptide linkage occurs in aromatic N- and C-protected dipeptides upon exposure to the environmental pollutants NO2[radical dot] and O3.
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Enantioselective total syntheses of the proposed structures of prevezol B and evaluation of anti-cancer activity

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8239-8246
DOI: 10.1039/C4OB01662A, PaperAnna E. Leung, Riccardo Rubbiani, Gilles Gasser, Kellie L. Tuck
The first enantioselective total syntheses of the proposed structures of the natural product prevezol B are reported. This work has shown that the proposed structures of prevezol B are incorrect.
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Investigation of desilylation in the recognition mechanism to fluoride by a 1,8-naphthalimide derivative

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8275-8279
DOI: 10.1039/C4OB01500B, PaperJeeun Woo, Gunwoo Kim, Kevanie Quintero, Michael P. Hanrahan, Hector Palencia, Haishi Cao
Desilylation based fluorescence sensor (AF-1) gives a dual signal for quantitative detection of F- in MeCN.
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Annulated and bridged tetrahydrofurans from alkenoxyl radical cyclization

10 October, 2014 - 05:54

Org. Biomol. Chem., 2014, 12,8288-8307
DOI: 10.1039/C4OB01266F, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Christine Schur, Harald Kelm, Thomas Gottwald, Arne Ludwig, Rainer Kneuer, Jens Hartung
4-Pentenoxyl radicals sharing two or more carbon atoms with a cycloalkane cyclize in a predictable manner stereoselectively and regioselectively to afford in solutions of bromotrichloromethane cycloalkyl-fused or -bridged 2-bromomethyltetrahydrofurans in up to 95% yield.
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