European Journal of Organic Chemistry

Cover image for Vol. 2013 Issue 6

February 2013

Volume 2013, Issue 6

Pages 1015–1172

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Addendum/Correction
    1. You have free access to this content
      Total Synthesis and Structure Confirmation of Cryptocaryol A (Eur. J. Org. Chem. 6/2013)

      D. Srinivas Reddy and Debendra K. Mohapatra

      Article first published online: 14 FEB 2013 | DOI: 10.1002/ejoc.201390012

      Thumbnail image of graphical abstract

      The cover picture shows the coincidence of our entry into genetic chemistry and the genetic chemistry laboratory at CSIR-IICT. In this article, we have achieved the first total synthesis and structure confirmation of Cryptocaryol A, a new structural class of programmed cell death 4 (Pdcd4) stablizing natural product, by combining Maruoka asymmetric allylation, Reetz chelation-controlled 1,3-induced allylation, Bartlett–Smith iterative iodocyclization and ring-closing metathesis reactions. Details are discussed in the article by D. S. Reddy and D. K. Mohapatra on p. 1051 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Addendum/Correction
    1. Graphical Abstract: Eur. J. Org. Chem. 6/2013 (pages 1015–1020)

      Article first published online: 14 FEB 2013 | DOI: 10.1002/ejoc.201390014

  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Addendum/Correction
  4. Microreview

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Addendum/Correction
    1. Hydroalkoxylation

      Coinage Metal Catalysts for the Addition of O–H to C=C Bonds (pages 1027–1039)

      Elena M. Barreiro, Luis A. Adrio, King Kuok (Mimi) Hii and John B. Brazier

      Article first published online: 29 JAN 2013 | DOI: 10.1002/ejoc.201201441

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      The direct addition of O–H bonds to C=C bonds is an attractive way to synthesise alcohols, ethers and esters. This microreview addresses the use of group 11 metals in promoting these transformations. The involvement of Brønsted acid catalysis in some of these reactions is highlighted.

  5. Short Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Addendum/Correction
    1. Chiral Organocatalysts

      BINOL-Fused Maleimides – A New Class of C2-Symmetric Chiral Imides (pages 1041–1045)

      Simon Brenet, Benoit Baptiste, Christian Philouze, Florian Berthiol and Jacques Einhorn

      Article first published online: 24 JAN 2013 | DOI: 10.1002/ejoc.201201525

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      The first synthesis of BINOL-fused maleimides has been achieved. This type of new chiral scaffold can be easily obtained from various BINOL analogues and 2,3-dihalomaleimide derivatives under basic conditions and can be easily functionalized on the BINOL moiety. BINOL-fused maleimides are promising new classes of chiral organocatalysts and ligands.

    2. Mannich Reaction

      Decarboxylative Mannich Reactions (pages 1046–1049)

      Maximillian Böhm, Kerstin Proksch and Rainer Mahrwald

      Article first published online: 24 JAN 2013 | DOI: 10.1002/ejoc.201201644

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      The results of catalyst-free, decarboxylative Mannich reactions of enolizable imines are described. When the reaction is performed with imines obtained from chiral aldehydes, access to optically pure Mannich products is possible.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Addendum/Correction
    1. Asymmetric Synthesis

      Total Synthesis and Structure Confirmation of Cryptocaryol A (pages 1051–1057)

      D. Srinivas Reddy and Debendra K. Mohapatra

      Article first published online: 19 DEC 2012 | DOI: 10.1002/ejoc.201201309

      Thumbnail image of graphical abstract

      Maruoka asymmetric allylation, chelation-controlled 1,3-induced allylation, iterative iodocyclization and ring-closing metathesis reactions were used sequentially to achieve the first total synthesis and structure confirmation of cryptocaryol A.

    2. Phosphonylation of N-Heterocycles

      Diphosphonylation of Aromatic Diazaheterocycles and Theoretical Rationalization of Product Yields (pages 1058–1067)

      Ann De Blieck, Saron Catak, Wouter Debrouwer, Józef Drabowicz, Karen Hemelsoet, Toon Verstraelen, Michel Waroquier, Veronique Van Speybroeck and Christian V. Stevens

      Article first published online: 14 JAN 2013 | DOI: 10.1002/ejoc.201201437

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      Diphosphonylated diazaheterocyclic compounds are synthesized in a one-step reaction from naphthyridines and phenanthrolines by using dimethyl trimethylsilyl phosphite (DMPTMS). The substrate has a profound influence on the product yields for the tandem 1,4–1,2-addition. The product yields are theoretically rationalized by evaluating proton affinities, aromaticities and free energies of activation.

      Corrected by:

      Correction: Diphosphonylation of Aromatic Diazaheterocycles and Theoretical Rationalization of Product Yields

      Vol. 2013, Issue 34, 7833–7834, Article first published online: 29 OCT 2013

    3. Drug Design

      Imidazole- and Benzimidazole-Based Inhibitors of the Kinase IspE: Targeting the Substrate-Binding Site and the Triphosphate-Binding Loop of the ATP Site (pages 1068–1079)

      Paolo Mombelli, Camille Le Chapelain, Noah Munzinger, Evelyne Joliat, Boris Illarionov, W. Bernd Schweizer, Anna K. H. Hirsch, Markus Fischer, Adelbert Bacher and François Diederich

      Article first published online: 4 JAN 2013 | DOI: 10.1002/ejoc.201201467

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      Inhibitors of the kinase E. coli IspE, an enzyme involved in the synthesis of isoprenoids and a model for IspE from P. falciparum, were developed. Decorated imidazole- and benzimidazole-based scaffolds address the cytidine-binding pocket, the hydrophobic sub-pocket, and the phosphate-binding region in the active site. In vitro activities in the micromolar IC50-range were measured.

    4. Peptide Binders

      Ditopic Arginine-Aspartate Binders Recognize RGD Loops (pages 1080–1092)

      Thomas Gersthagen, Johannes Hofmann, Frank-Gerrit Klärner, Carsten Schmuck and Thomas Schrader

      Article first published online: 7 JAN 2013 | DOI: 10.1002/ejoc.201201052

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      Both binding sites of the ditopic molecular tweezers bind arginine–glycine–aspartate (RGD) loops (Kd ≈ 20 μM in buffer), but not by inclusion inside the cavity of the tweezers.

    5. Amino Acids

      Synthesis of Racemic δ,δ-Dimethylproline Derivatives (pages 1093–1099)

      Isabel Rodríguez, M. Isabel Calaza and Carlos Cativiela

      Article first published online: 11 JAN 2013 | DOI: 10.1002/ejoc.201201420

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      δ,δ-Dimethylproline derivatives have been efficiently synthesized by employing a β-amino acid as the starting material. The methodology is amenable to the preparation of other δ,δ-disubstituted prolines.

    6. Alkaloid Total Synthesis

      Total Synthesis of the Spirocyclic Oxindole Alkaloids Corynoxine, Corynoxine B, Corynoxeine, and Rhynchophylline (pages 1100–1106)

      Martin J. Wanner, Steen Ingemann, Jan H. van Maarseveen and Henk Hiemstra

      Article first published online: 7 JAN 2013 | DOI: 10.1002/ejoc.201201505

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      Racemic total syntheses of the four title spirocyclic oxindole alkaloids are reported starting from 4-hydroxytryptamine. The key steps were a base-mediated Mannich spirocyclisation to form the C-ring, and a Pd-catalysed cyclisation of a keto ester enolate onto an allylic carbonate to form the D-ring. Thus, convenient syntheses of the alkaloids were achieved, for three of them for the first time.

    7. Alkaloid Synthesis

      A Route to Azafluoranthene Natural Products Through Direct Arylation (pages 1107–1115)

      Shashikanth Ponnala and Wayne W. Harding

      Article first published online: 3 JAN 2013 | DOI: 10.1002/ejoc.201201190

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      Microwave-assisted direct arylation reactions were successfully employed in the synthesis of azafluoranthene alkaloids for the first time. Rufescine and triclisine were efficiently prepared using this method. The method has broader applicability in the synthesis of structurally similar tetracyclic isoquinoline alkaloids.

    8. Tubulin-Binding Molecules

      Synthesis and Biological Evaluation of α-Tubulin-Binding Pironetin Analogues with Enhanced Lipophilicity (pages 1116–1123)

      Miguel Carda, Juan Murga, Santiago Díaz-Oltra, Jorge García-Pla, Julián Paños, Eva Falomir, Chiara Trigili, J. Fernando Díaz, Isabel Barasoain and J. Alberto Marco

      Article first published online: 7 JAN 2013 | DOI: 10.1002/ejoc.201201283

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      The preparation of four new analogues of the natural pyrone pironetin, known to bind to α-tubulin, is described. The C9 side-chain of pironetin has been replaced in one analogue by a 4-phenylbutyl chain and in the other three analogues by C13 or C16 aliphatic chains, all of them bearing two stereogenic centres. Their cytotoxic activities and interactions with tubulin have been investigated.

    9. Natural Product Synthesis

      Synthetic Studies on the Nhatrangins: Stereoselective Access to an Advanced Aldehyde Intermediate (pages 1124–1131)

      Ludovic Raffier and Olivier Piva

      Article first published online: 16 JAN 2013 | DOI: 10.1002/ejoc.201201338

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      Two strategies have been considered for the stereoselective synthesis of nhatrangins A and B. A sequence involving diastereoselective alkylation and aldolization employing ephedrine derivatives as chiral auxiliaries was the most efficient approach to deliver a key aldehyde framework.

    10. Vinyl Cations

      Regiocontrolled Hydroarylation of (Trifluoromethyl)acetylenes in Superacids: Synthesis of CF3-Substituted 1,1-Diarylethenes (pages 1132–1143)

      Haider M. H. Alkhafaji, Dmitry S. Ryabukhin, Vasiliy M. Muzalevskiy, Aleksander V. Vasilyev, Georgy K. Fukin, Alexey V. Shastin and Valentine G. Nenajdenko

      Article first published online: 7 JAN 2013 | DOI: 10.1002/ejoc.201201375

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      The superacidic generation of vinyl cations from aryl(trifluoromethyl)acetylenes was effectively performed using triflic and fluorosulfonic acids under mild conditions. These vinyl cations underwent a subsequent reaction with various arenes to give the corresponding alkenes and alcohols in high yields. The formation of these trifluoroethylated carbocations was confirmed by NMR spectroscopy.

    11. Photoinduced Reactions

      Thiyl Glycosylation of Propargylated Octasilsesquioxane: Synthesis and Lectin-Binding Properties of Densely Glycosylated Clusters on a Cubic Platform (pages 1144–1149)

      Alberto Marra, Samuele Staderini, Nathalie Berthet, Pascal Dumy, Olivier Renaudet and Alessandro Dondoni

      Article first published online: 14 JAN 2013 | DOI: 10.1002/ejoc.201201453

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      Typical hexadecavalent glyco-POSS prepared by thiol-yne coupling. A measured IC50 of 2 nM was found by ELLA with tetrameric wheat germ agglutinin (WGA).

    12. C–H Bond Activation

      Ruthenium-Catalyzed Selective Aerobic Oxidative ortho-Alkenylation of Substituted Phenols with Alkenes through C–H Bond Activation (pages 1150–1157)

      Mallu Chenna Reddy and Masilamani Jeganmohan

      Article first published online: 10 JAN 2013 | DOI: 10.1002/ejoc.201201463

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      The oxidative coupling of substituted phenyl carbamates and acetates with alkenes in the presence of [RuCl2(p-cymene)]2, AgSbF6, and Cu(OAc)2·H2O provided substituted alkene derivatives in a highly regio- and stereoselective manner. In the presence of either LiOH·H2O or K2CO3, ortho-alkenylated phenyl carbamates and acetates were converted into the corresponding phenols.

    13. DNA Damage

      Synthesis of Site-Specific Damaged DNA Strands by 8-(Acetylarylamino)-2′-deoxyguanosine Adducts and Effects on Various DNA Polymerases (pages 1158–1169)

      Sarah Krüger and Chris Meier

      Article first published online: 10 JAN 2013 | DOI: 10.1002/ejoc.201200984

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      C8-NAc-Arylamine adducts of 2′-deoxyguanosine with various aromatic amines were synthesized by using cross-coupling reactions and converted into 3′-phosphoramidites. Site-specific damaged NarI-, EcoRI- and 20mer-oligonucleotides were prepared by automated DNA-synthesis. Biophysical properties, restriction endonuclease studies and DNA-polymerase assays were performed.

  7. Addendum/Correction

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Addendum/Correction
    1. You have free access to this content
      Diels–Alder Reactions for the Construction of Cyclopropylarenes (pages 1171–1172)

      Marion Arndt, Gerhard Hilt, Alexander F. Khlebnikov, Sergei I. Kozhushkov and Armin de Meijere

      Article first published online: 21 JAN 2013 | DOI: 10.1002/ejoc.201201724

      This article corrects:

      Diels–Alder Reactions for the Construction of Cyclopropylarenes1

      Vol. 2012, Issue 16, 3112–3121, Article first published online: 17 APR 2012

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