Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Synthesis of 1-amino-2-aroyl/acetylnaphthalenes through a base mediated one pot inter and intramolecular C-C bond formation strategy

17 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4730-4737
DOI: 10.1039/C4OB00432A, PaperSurjeet Singh, Pratik Yadav, Satya Narayan Sahu, Ismail Althagafi, Abhinav Kumar, Brijesh Kumar, Vishnu Ji Ram, Ramendra Pratap
Base mediated synthesis of highly functionalized aroyl/acetylnaphthalenes by the reaction of 2-(1-cyano-2,2-bis(methylthio)vinyl)benzonitrile and aryl methyl ketone or acetone has been reported.
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Interaction of amphiphilic [small alpha]-helical cell-penetrating peptides with heparan sulfate

17 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4673-4681
DOI: 10.1039/C4OB00673A, PaperJi Yang, Hiroshi Tsutsumi, Tadaomi Furuta, Minoru Sakurai, Hisakazu Mihara
The binding of cell-penetrating peptides to heparan sulfate is investigated experimentally and computationally.
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Acetal-initiated Prins bicyclization for the synthesis of hexahydrofuro-[3,4-c]furan lignans and octahydropyrano[3,4-c]pyran derivatives

17 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4754-4762
DOI: 10.1039/C4OB00305E, PaperB. V. Subba Reddy, M. Ramana Reddy, B. Sridhar, Kiran Kumar Singarapu
The stereoselective synthesis of hexahydrofuro[3,4-c]furan lignans and octahydropyrano[3,4-c]pyran derivatives is reported through a Prins bicyclization.
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Marine bacteria from the Roseobacter clade produce sulfur volatiles via amino acid and dimethylsulfoniopropionate catabolism

15 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4318-4323
DOI: 10.1039/C4OB00719K, CommunicationNelson L. Brock, Markus Menke, Tim A. Klapschinski, Jeroen S. Dickschat
The biosynthesis of sulfur volatiles in marine bacteria was studied by feeding of 34S-labelled DMSP and some unnatural derivatives.
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N,N-Dimethylaminobenzoates enable highly enantioselective Sharpless dihydroxylations of 1,1-disubstituted alkenes

15 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4314-4317
DOI: 10.1039/C4OB00621F, CommunicationYaohong Zhao, Xiangyou Xing, Shaolong Zhang, David Zhigang Wang
Exploration of beneficial catalyst-substrate interactions in the classical Sharpless asymmetric dihydroxylations (SAD) led to the identification of allylic N,N-dimethylaminobenzoate as an efficient auxiliary for inducing high levels of enantioselectivity in 1,1-disubstituted aliphatic alkenes.
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An iterative in silico and modular synthetic approach to aqueous soluble tercyclic [small alpha]-helix mimetics

15 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4432-4444
DOI: 10.1039/C4OB00647J, PaperZelong Lim, Peter J. Duggan, Adam G. Meyer, Kellie L. Tuck
Tercyclic scaffolds, designed to have improved synthetic accessibility and aqueous solubility, were evaluated as structural [small alpha]-helix mimetics by using an iterative in silico approach.
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Novel one-pot synthesis of diverse [gamma],[small delta]-unsaturated [small beta]-ketoesters by thermal cascade reactions of diazodicarbonyl compounds and enol ethers: transformation into substituted 3,5-diketoesters

15 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4407-4411
DOI: 10.1039/C4OB00664J, PaperRameshwar Prasad Pandit, Yong Rok Lee
Novel and efficient synthesis of diverse [gamma],[small delta]-unsaturated [small beta]-ketoesters was accomplished by thermal cascade reactions of diazodicarbonyl compounds with enol ethers and the synthesized compounds were further transformed into the corresponding 3,5-diketoesters.
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Catalyst-controlled regio- and stereoselective synthesis of diverse 12H-6,12-methanodibenzo[d,g][1,3]dioxocines

13 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4386-4396
DOI: 10.1039/C4OB00691G, PaperLikai Xia, Hongyun Cai, Yong Rok Lee
Regio- and stereoselective synthesis of 12H-6,12-methanodibenzo[d,g][1,3]dioxocines has been accomplished by the EDDA and PTSA-catalyzed cascade reactions of resorcinols and 2-hydroxychalcones.
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A succinyl lysine-based photo-cross-linking peptide probe for Sirtuin 5

13 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4310-4313
DOI: 10.1039/C4OB00773E, CommunicationKarunakaran A. Kalesh, Edward W. Tate
A succinylation-specific photo-cross-linking peptide probe has been developed for the NAD+-dependent hydrolase Sirtuin 5.
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Transition-metal-free oxidative carboazidation of acrylamides via cascade C-N and C-C bond-forming reactions

13 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4329-4334
DOI: 10.1039/C4OB00720D, CommunicationJun Qiu, Ronghua Zhang
A novel transition-metal-free oxidative carboazidation of acrylamides using inexpensive NaN3 and K2S2O8 was achieved, which not only provided an efficient method to prepare various N3-substituted oxindoles, but also represented a novel strategy for C-N and C-C bond formation via a free-radical cascade process.
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Development of a PET radiotracer for non-invasive imaging of the reactive oxygen species, superoxide, in vivo

13 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4421-4431
DOI: 10.1039/C3OB42379D, PaperWenhua Chu, Andre Chepetan, Dong Zhou, Kooresh I. Shoghi, Jinbin Xu, Laura L. Dugan, Robert J. Gropler, Mark A. Mintun, Robert H. Mach
Non-invasive imaging of reactive oxygen species (ROS) in vivo was investigated using a dihydroethidium analog [18F]12 as a PET radiotracer. The data shown indicates that [18F]12 is a promising PET tracer for non-invasive imaging of ROS in vivo.
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A chemoselective oxidation of monosubstituted ethylene glycol: facile synthesis of optically active [small alpha]-hydroxy acids

13 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4305-4309
DOI: 10.1039/C4OB00601A, CommunicationKiran Chinthapally, Sundarababu Baskaran
A mild and efficient method for the chemoselective oxidation of monosubstituted ethylene glycols to optically active [small alpha]-hydroxy acids has been achieved using the TEMPO-NaOCl reagent system.
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Bronsted acid mediated nitrogenation of propargylic alcohols: an efficient approach to alkenyl nitriles

13 June, 2014 - 01:17

Org. Biomol. Chem., 2014, 12,4324-4328
DOI: 10.1039/C4OB00888J, CommunicationXiaoqiang Huang, Ning Jiao
A novel and efficient approach to alkenyl nitriles from readily available propargylic alcohols has been developed.
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CuI catalyzed sulfonylation of organozinc reagents with sulfonyl halides

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4295-4299
DOI: 10.1039/C4OB00638K, CommunicationYing Fu, Wenbo Zhu, Xingling Zhao, Helmut Hugel, Zhouqiang Wu, Yuhu Su, Zhengyin Du, Danfeng Huang, Yulai Hu
A general and efficient CuI/TMEDA catalyzed nucleophilic addition of functionalized organozinc reagents to organic sulfonyl chlorides has been developed for both aromatic and aliphatic sulfone synthesis.
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Nanomolar fluorogenic detection of Al(III) by a series of Schiff bases in an aqueous system and their application in cell imaging

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4445-4453
DOI: 10.1039/C4OB00329B, PaperSanyog Sharma, Maninder Singh Hundal, Amandeep Walia, Vanita Vanita, Geeta Hundal
Three Schiff bases, showing nanomolar, naked eye detection of Al(III) under UV light, in an aqueous system are reported.
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Asymmetric synthesis of tetrahydroquinolines through supramolecular organocatalysis

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4300-4304
DOI: 10.1039/C4OB00570H, CommunicationDhevalapally B. Ramachary, Kodambahalli S. Shruthi
Functionalized chiral tetrahydroquinolines were synthesized through supramolecular organocatalysis using quinidine-NH-thiourea 3c/L-phenylalanine 4i followed by reductive amination from the simple substrates.
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A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4397-4406
DOI: 10.1039/C4OB00515E, PaperMitsuru Kitamura, So Kato, Masakazu Yano, Norifumi Tashiro, Yuichiro Shiratake, Mitsuyoshi Sando, Tatsuo Okauchi
Organic azides were synthesized from primary amines by diazo-transfer with a safe and stable crystalline reagent, 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP).
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Efficient one-step synthesis of 4-amino substituted phthalimides and evaluation of their potential as fluorescent probes

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4461-4470
DOI: 10.1039/C4OB00342J, PaperTomas Kindahl, Erik Chorell
Chemistry: One step, high yields, general, atom efficient, no additives. Compounds: Highly fluorescent and solvatochromic, many display non-toxic properties.
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A stereoselective approach to indolizidine and pyrrolizidine alkaloids: total synthesis of (-)-lentiginosine, (-)-epi-lentiginosine and (-)-dihydroxypyrrolizidine

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4454-4460
DOI: 10.1039/C4OB00461B, PaperShruti Vandana Kauloorkar, Vishwajeet Jha, Ganesh Jogdand, Pradeep Kumar
The total synthesis of (-)-lentiginosine, epi-1,2-lentiginosine and dihydroxypyrrolizidine is reported from an aldehyde as a starting material using organocatalysis and asymmetric dihydroxylation as key steps.
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Organocatalytic enantioselective construction of multi-functionalized spiro oxindole dienes

11 June, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,4372-4385
DOI: 10.1039/C4OB00545G, PaperXiao-Fei Huang, Ya-Fei Zhang, Zheng-Hang Qi, Nai-Kai Li, Zhi-Cong Geng, Kun Li, Xing-Wang Wang
A highly stereoselective Michael-cyclization-tautomerization reaction of isatylidene malononitriles with [small alpha],[small alpha]-dicyanoalkenes was developed via organocatalysis. An anomalous temperature effect on the enantioselectivity is disclosed for this transformation.
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