Org. and Biomol. Chem.

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Synthesis, structural characterization and biological activity of two diastereomeric JA-Ile macrolactones

26 May, 2015 - 14:54

Org. Biomol. Chem., 2015, 13,5885-5893
DOI: 10.1039/C5OB00362H, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Guillermo H. Jimenez-Aleman, Ricardo A. R. Machado, Helmar Gorls, Ian T. Baldwin, Wilhelm Boland
The synthesis and biological activity of two diastereomeric macrolactones derived from the partially inactive jasmonate 12-OH-JA-Ile are discussed. Both diastereoisomers induce nicotine production similar to methyl jasmonate in Nicotiana attenuata plants.
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New Dimeric Carbazole-Benzimidazole Mixed Ligands for the Stabilization of Human Telomeric G-Quadruplex DNA and as Telomerase Inhibitors. Remarkable Influence of Spacer

24 May, 2015 - 14:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00675A, PaperBasudeb Maji, Krishan Kumar, K Muniyappa, Santanu Bhattacharya
The development of G-quadruplex (G4) DNA binding small molecules has become an important strategy for targeting cancer cells selectively. Herein, we report the design and evolution of a new kind...
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BINOL-Al catalysed asymmetric cyclization and amplification: preparation of optically active menthol analogs

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5817-5825
DOI: 10.1039/C5OB00433K, PaperHisanori Itoh, Hironori Maeda, Shinya Yamada, Yoji Hori, Takashi Mino, Masami Sakamoto
We report a highly selective asymmetric ring-closing ene reaction catalyzed by chiral aluminum complexes. Asymmetric amplification of this reaction was investigated by varying the ee of the BINOL employed in the catalyst.
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Effect of preorganization on the affinity of synthetic DNA binding motifs for nucleotide ligands

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5734-5742
DOI: 10.1039/C5OB00508F, PaperS. Vollmer, C. Richert
Triple helices with an abasic bridge between two oligopurine segments bind ligands like ATP, FAD, and cAMP with dissociation constants as low as 30 nM.
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Carbonic anhydrase II as host protein for the creation of a biocompatible artificial metathesase

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5652-5655
DOI: 10.1039/C5OB00428D, PaperJingming Zhao, Anna Kajetanowicz, Thomas R. Ward
We report an efficient artificial metathesase which combines an arylsulfonamide anchor within the protein scaffold human carbonic anhydrase II.
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Direct conversion of allyl arenes to aryl ethylketones via a TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5613-5616
DOI: 10.1039/C5OB00586H, CommunicationJinWu Zhao, Li Liu, ShiJian Xiang, Qiang Liu, HuoJi Chen
A TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes was developed.
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Palladium-catalyzed asymmetric allylic amination of racemic butadiene monoxide with isatin derivatives

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5826-5830
DOI: 10.1039/C5OB00663E, PaperGen Li, Xiangqing Feng, Haifeng Du
Pd-catalyzed asymmetric aminations of butadiene monoxide with isatin derivatives using P/alkene ligands gave high yields, ees and regioselectivity ratios.
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Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5793-5803
DOI: 10.1039/C5OB00541H, PaperAli H. Essa, Reinner I. Lerrick, Ece Ciftci, Ross W. Harrington, Paul G. Waddell, William Clegg, Michael J. Hall
2,2,2-Trichloro-1-aryl-ethanones can be reduced by RMgX to the corresponding 2,2-dichloro-1-arylethen-1-olates and trapped with a range of electrophiles. In addition we demonstrate that 2,2-dichloro-1-arylethen-1-olates undergo counter-ion controlled Darzens condensations.
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Tri- and tetra-substituted cyclen based lanthanide(III) ion complexes as ribonuclease mimics: a study into the effect of log Ka, hydration and hydrophobicity on phosphodiester hydrolysis of the RNA-model 2-hydroxypropyl-4-nitrophenyl phosphate (HPNP)

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5804-5816
DOI: 10.1039/C4OB02384F, PaperAnn-Marie Fanning, Sally. E. Plush, Thorfinnur Gunnlaugsson
Lanthanide(III) complexes of 'pseudo' dipeptide ligands and 3'-pyridine ligands have been characterised as metallo-ribonuclease mimics.
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Direct synthesis of a geminal zwitterionic phosphonium/hydridoborate system - developing an alternative tool for generating frustrated Lewis pair hydrogen activation systems

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5783-5792
DOI: 10.1039/C5OB00634A, PaperJiangang Yu, Gerald Kehr, Constantin G. Daniliuc, Christoph Bannwarth, Stefan Grimme, Gerhard Erker
A convenient way to a new class of geminal Mes2PH+/B(C6F5)2H- pairs is presented.
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Simultaneous introduction of trifluoromethyl and [small lambda]6-pentafluorosulfanyl substituents using F5S-C[triple bond, length as m-dash]C-CF3 as a dienophile

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5625-5628
DOI: 10.1039/C5OB00610D, CommunicationBlazej Duda, Dieter Lentz
SF5-C[triple bond, length as m-dash]C-CF3 as a powerful dienophile in Diels-Alder reactions, provides the corresponding products in up to quantitative yields and allows the introduction of the pentafluorosulfanyl group and trifluoromethyl group at the 1,2 position.
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Fluorine containing amino acids: synthesis and peptide coupling of amino acids containing the all-cis tetrafluorocyclohexyl motif

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5621-5624
DOI: 10.1039/C5OB00650C, CommunicationMohammed Salah Ayoup, David B. Cordes, Alexandra M. Z. Slawin, David O'Hagan
A synthesis of amino acids carrying the all-cis tetrafluorocyclohexyl ring moiety is demonstrated and protection/deprotection elaborations are illustrated which show that this facially polarised ring motif may be incorporated into peptides.
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Binaphthyl-1,2,3-triazole peptidomimetics with activity against Clostridium difficile and other pathogenic bacteria

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5743-5756
DOI: 10.1039/C5OB00576K, PaperSteven M. Wales, Katherine A. Hammer, Amy M. King, Andrew J. Tague, Dena Lyras, Thomas V. Riley, Paul A. Keller, Stephen G. Pyne
Designed binaphthyl-based, cationic peptidomimetic antimicrobials targeting C. difficile, incorporating a click-derived 1,2,3-triazole ester isostere at the C-terminus MICs of 4 [small mu ]g mL-1 against three human isolates of C. difficile.
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Synthetic studies toward the brasilinolides: controlled assembly of a protected C1-C38 polyol based on fragment union by complex aldol reactions

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5716-5733
DOI: 10.1039/C5OB00498E, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Ian Paterson, Michael P. Housden, Christopher J. Cordier, Paul M. Burton, Friedrich A. Muhlthau, Olivier Loiseleur
A modular strategy for the synthesis of the immunosuppressant macrolide brasilinolide A was adopted based on coupling suitable northern and southern fragments.
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Copper-catalyzed aerobic oxidative amination of C(sp3)-H bonds: synthesis of imidazo[1,5-a]pyridines

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5602-5607
DOI: 10.1039/C5OB00381D, CommunicationDarapaneni Chandra Mohan, Sadu Nageswara Rao, Chitrakar Ravi, Subbarayappa Adimurthy
Copper-catalyzed synthesis of imidazo[1,5-a]pyridine-1-carboxylates through oxidative amination of C(sp3)-H bonds under mild aerobic conditions with broad substrate scope has been achieved.
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A preorganized [small beta]-amino acid bearing a guanidinium side chain and its use in cell-penetrating peptides

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5617-5620
DOI: 10.1039/C5OB00389J, CommunicationYosuke Demizu, Makoto Oba, Koyo Okitsu, Hiroko Yamashita, Takashi Misawa, Masakazu Tanaka, Masaaki Kurihara, Samuel H. Gellman
A cyclic [small beta]-amino acid (APCGu) bearing a side-chain guanidinium group has been developed.
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High solid-state luminescence in propeller-shaped AIE-active pyridine-ketoiminate-boron complexes

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5775-5782
DOI: 10.1039/C5OB00607D, PaperYanping Wu, Zhenyu Li, Qingsong Liu, Xiaoqing Wang, Hui Yan, Shuwen Gong, Zhipeng Liu, Weijiang He
Two pyridine-ketoiminate-based organoboron complexes were demonstrated to possess aggregation-induced emission, large Stokes shift and high quantum yield in the solid-state, which were rationalized through X-ray crystal analysis and electronic structure calculations.
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Indium-catalyzed oxidative cross-dehydrogenative coupling of chromenes with 1,3-dicarbonyls and aryl rings

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5710-5715
DOI: 10.1039/C5OB00277J, PaperFanmei Li, Zhilin Meng, Jing Hua, Wei Li, Hongxiang Lou, Lei Liu
An efficient indium-catalyzed oxidative cross-dehydrogenative coupling of chromenes with 1,3-dicarbonyls and aryl rings promoted by DDQ was described.
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Organocatalytic regioselective asymmetric Michael addition of azlactones to o-hydroxy chalcone derivatives

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5698-5709
DOI: 10.1039/C5OB00121H, PaperShao-Yun Zhang, Gui-Yu Ruan, Zhi-Cong Geng, Nai-Kai Li, Ming Lv, Yong Wang, Xing-Wang Wang
Regio- and enantio-selective Michael addition between azlactones with o-hydroxy chalcone derivatives is reported. Optically active N,O-aminals are obtained in good yields with good to excellent diastereo- and enantio-selectivities.
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Stereoselective construction of functionalized tetracyclic and pentacyclic coumarinopyranpyrazole/pyrimidinedione/coumarin scaffolds using a solid-state melt reaction

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5597-5601
DOI: 10.1039/C5OB00442J, CommunicationManickam Bakthadoss, Damodharan Kannan, Nagappan Sivakumar, Palani Malathi, Vasudevan Manikandan
An assembly of tetra / pentacyclic hybrid scaffolds have been synthesized for the first time using a solid-state melt reaction in a stereoselective fashion with excellent yields.
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