European Journal of Organic Chemistry

Cover image for Vol. 2014 Issue 22

August 2014

Volume 2014, Issue 22

Pages 4675–4903

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. You have free access to this content
      Total Synthesis of (+)-Antimycin A3b on Solid Supports (Eur. J. Org. Chem. 22/2014)

      Yusuke Iijima, Osamu Kimata, Santida Decharin, Hisashi Masui, Yoichiro Hirose and Takashi Takahashi

      Article first published online: 22 JUL 2014 | DOI: 10.1002/ejoc.201490060

      Thumbnail image of graphical abstract

      The cover picture shows a straightforward total synthesis of (+)-antimycin A3b. Four fragments were assembled on a solid support, and the fully functionalized seco acid was cyclized in the solution phase. This convergent synthetic route is useful, because it minimizes the number of manipulations in the solution phase and is hence suitable for a combinatorial library synthesis. Details are discussed in the article by T. Takahashi et al. on p. 4725 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. Correction
    1. Graphical Abstract: Eur. J. Org. Chem. 22/2014 (pages 4675–4682)

      Article first published online: 22 JUL 2014 | DOI: 10.1002/ejoc.201490062

  3. News

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

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

      Evolution of BODIPY Dyes as Potential Sensitizers for Dye-Sensitized Solar Cells (pages 4689–4707)

      Surya Prakash Singh and Thumuganti Gayathri

      Article first published online: 16 MAY 2014 | DOI: 10.1002/ejoc.201400093

      Thumbnail image of graphical abstract

      Harnessing maximum light from the solar spectrum is the key to improve photovoltaic performance of solar cells. Possessing outstanding photophysical properties and flexibility in structural modification, BODIPY dyes have emerged as potential sensitizers for Dye-Sensitized Solar Cells (DSSCs).

  5. Short Communications

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

      Kinetic Data on the Synergetic Role of Amines and Water in the Reduction of Phosphine-Ligated Palladium(II) to Palladium(0) (pages 4709–4713)

      Christian Amatore, Laurent El Kaïm, Laurence Grimaud, Anny Jutand, Alice Meignié and Georgy Romanov

      Article first published online: 25 JUN 2014 | DOI: 10.1002/ejoc.201402519

      Thumbnail image of graphical abstract

      A Pd0 complex is formed from [PdCl2(PPh3)2] through the synergetic role of water and amine (which generates hydroxide ions) in an intramolecular reduction occurring in [PdCl(OH)(PPh3)2]. The ligated phosphine is the reducing agent.

    2. Practical Synthesis

      Enantioselective Synthesis of Tetrahydrofuran Derivatives by Sequential Henry Reaction and Iodocyclization of γ,δ-Unsaturated Alcohols (pages 4714–4719)

      Li-Yan Chen, Jia-Rong Chen, Hong-Gang Cheng, Liang-Qiu Lu and Wen-Jing Xiao

      Article first published online: 26 JUN 2014 | DOI: 10.1002/ejoc.201402396

      Thumbnail image of graphical abstract

      By using a combination of Cu(OAc)2·H2O and a novel chiral sulfoxide–Schiff base hybrid ligand, useful 2,2,5-trisubstituted tetrahydrofuran derivatives are prepared through a one-pot asymmetric Henry reaction/iodocyclization sequence. A wide range of substrates is tolerated, and the products are generally obtained in high yields with excellent enantioselectivities.

    3. C–H Amination

      Facile Access to 1H-Indazoles through Iodobenzene-Catalyzed C–H Amination under Mild, Transition-Metal-Free Conditions (pages 4720–4723)

      Mitsuhiro Kashiwa, Motohiro Sonoda and Shinji Tanimori

      Article first published online: 30 JUN 2014 | DOI: 10.1002/ejoc.201402488

      Thumbnail image of graphical abstract

      Transition-metal- and halogen-free synthesis of N-aryl-substituted 1H-indazole and derivatives is accomplished on the basis of the iodobenzene-catalyzed intramolecular C–H amination of hydrazones in the presence of Oxone in trifluoroacetic acid at –10 °C. The 1H-indazole derivatives are obtained in moderate to good yields (up to 90 %).

  6. Full Papers

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

      Total Synthesis of (+)-Antimycin A3b on Solid Supports (pages 4725–4732)

      Yusuke Iijima, Osamu Kimata, Santida Decharin, Hisashi Masui, Yoichiro Hirose and Takashi Takahashi

      Article first published online: 3 JUN 2014 | DOI: 10.1002/ejoc.201402430

      Thumbnail image of graphical abstract

      A straightforward and convergent total synthesis of (+)-antimycin A3b is reported. Four fragments were assembled on a solid support and the fully functionalized seco acid was cyclized in the solution phase. This synthetic route minimized the number of manipulations in the solution phase and is useful for a combinatorial library synthesis.

    2. Hydrosilylation

      Highly Regioselective Hydrosilylation of Unsymmetric Alkynes Using a Phenylthio Directing Group (pages 4733–4740)

      Kuan-Hsun Huang and Minoru Isobe

      Article first published online: 17 JUN 2014 | DOI: 10.1002/ejoc.201402577

      Thumbnail image of graphical abstract

      Cobalt-catalyzed hydrosilylation with unsymmetric propargylic alcohols is highly regioselective with phenylthioacetylenes. The phenylthio group acts as a directing group in this reaction exerting effects due to (i) steric interactions involving the alkyl group, and (ii) stereoelectronic effects.

    3. Total Synthesis

      Synthesis of 2-Hydroxy-7-methylcarbazole, Glycozolicine, Mukoline, Mukolidine, Sansoakamine, Clausine-H, and Clausine-K and Structural Revision of Clausine-TY (pages 4741–4752)

      Christian Schuster, Carsten Börger, Konstanze K. Julich-Gruner, Ronny Hesse, Anne Jäger, Györley Kaufmann, Arndt W. Schmidt and Hans-Joachim Knölker

      Article first published online: 17 JUN 2014 | DOI: 10.1002/ejoc.201402495

      Thumbnail image of graphical abstract

      A palladium-catalyzed oxidative cyclization has been applied to the total syntheses of the carbazole alkaloids 2-hydroxy-7-methylcarbazole, glycozolicine, mukoline, mukolidine, sansoakamine, glycozolidine, clausine-H (clauszoline-C), clausine-K (clauszoline-J), and methyl 2-hydroxy-7-methoxycarbazole-3-carboxylate. The synthesis of the latter led to the structural reassignment of clausine-TY.

    4. Plant Metabolites

      Merrilliadione – a Rare Isopropyl (13[RIGHTWARDS ARROW]11)-abeo-9,11-seco Abietane Diterpene from Illicium merrillianum (pages 4753–4758)

      Xinhui Tian, Rongcai Yue, Shoude Zhang, Yunheng Shen, Ji Ye, Lei Shan, Huiliang Li, Bo Wen, Xike Xu and Weidong Zhang

      Article first published online: 17 JUN 2014 | DOI: 10.1002/ejoc.201402406

      Thumbnail image of graphical abstract

      Merrilliadione (1), a diterpene with a unique isopropyl (13[RIGHTWARDS ARROW]11)-abeo-9,11-seco-abietane skeleton, and two the new abietane diterpenoids 2 and 3 were isolated from Illicium merrillianum. The structures of 13 were established by spectroscopic analysis, single-crystal X-ray diffraction, and quantum chemical computation of electronic circular dichroism (ECD) spectra.

    5. Anion Binding

      Synthesis, Solid-State Analyses, and Anion-Binding Properties of meso-Aryldipyrrin-5,5′-diylbis(phenol) and -bis(aniline) Ligands (pages 4759–4766)

      Laurent Copey, Ludivine Jean-Gérard, Eric Framery, Guillaume Pilet and Bruno Andrioletti

      Article first published online: 24 JUN 2014 | DOI: 10.1002/ejoc.201402446

      Thumbnail image of graphical abstract

      The synthesis and structural determination of a series of 5,5′-diaryldipyrromethenes is described. Solution analyses, X-ray crystal-structure determination, and anion-binding properties are used to rationalize the effect of the substituent on the dipyrromethene subunit.

    6. Cycloadditions

      Sterically Controlled Diels–Alder Cycloadditions: Rapid Entry into the Illudin Scaffold (pages 4767–4772)

      Lars Stevens-Cullinane, Nigel T. Lucas and Bill C. Hawkins

      Article first published online: 24 JUN 2014 | DOI: 10.1002/ejoc.201402461

      Thumbnail image of graphical abstract

      Access to the tricyclic core of the illudins was achieved using a sterically directed, regioselective Diels–Alder cycloaddition. The cycloaddition was found to proceed under relatively mild conditions and with a variety of cyclic and acyclic dienophiles.

    7. Domino Reactions

      Mechanistic Insights into the Palladium-Catalyzed Domino Synthesis of 10,11-Dihydro-5H-dibenzo[b,e][1,4]diazepines (pages 4773–4779)

      Joydev K. Laha, K. S. Satyanarayana Tummalapalli and Ankur Gupta

      Article first published online: 24 JUN 2014 | DOI: 10.1002/ejoc.201402207

      Thumbnail image of graphical abstract

      A domino approach to the synthesis of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines starting from o-phenylenediamines and 2-bromobenzyl bromides or tosylates has been developed. The reaction proceeds by a palladium-catalyzed intermolecular mono-N-benzylation of the o-phenylenediamine, followed by an intramolecular N′-arylation.

    8. Configuration Determination

      Assignment of the Absolute Configuration and Total Synthesis of (+)-Caripyrin (pages 4780–4784)

      Lars Andernach and Till Opatz

      Article first published online: 24 JUN 2014 | DOI: 10.1002/ejoc.201402540

      Thumbnail image of graphical abstract

      The absolute configuration of the natural product (+)-caripyrin was determined by vibrational circular dichroism spectroscopy and density functional theory calculations. Based on this information, the compound was prepared in a short asymmetric synthesis.

    9. Lipopeptide Synthesis

      Solid-Phase Synthesis of Cyclic Lipopeptidotriazoles (pages 4785–4794)

      Sílvia Vilà, Cristina Camó, Eduard Figueras, Esther Badosa, Emilio Montesinos, Marta Planas and Lidia Feliu

      Article first published online: 24 JUN 2014 | DOI: 10.1002/ejoc.201402111

      Thumbnail image of graphical abstract

      An efficient methodology for the solid-phase synthesis of cyclic lipopeptidotriazoles involving the use of five orthogonal protecting groups has been established. This strategy has been used to prepare a set of derivatives of the antimicrobial cyclic peptide BPC194 in high purities.

    10. Synthetic Methods

      Hypervalent Iodine(III)-Promoted Metal-Free S–H Activation: An Approach for the Construction of S–S, S–N, and S–C Bonds (pages 4795–4804)

      Eakkaphon Rattanangkool, Watanya Krailat, Tirayut Vilaivan, Preecha Phuwapraisirisan, Mongkol Sukwattanasinitt and Sumrit Wacharasindhu

      Article first published online: 24 JUN 2014 | DOI: 10.1002/ejoc.201402180

      Thumbnail image of graphical abstract

      Disulfides and sulfenamides can be easily prepared from the corresponding thiols by using (diacetoxyiodo)benzene as activator at room temperature under open-flask conditions.

    11. Structure Elucidation

      Structure Determination of Pentacyclic Pyridoacridine Alkaloids from the Australian Marine Organisms Ancorina geodides and Cnemidocarpa stolonifera (pages 4805–4816)

      Trong D. Tran, Ngoc B. Pham and Ronald J. Quinn

      Article first published online: 23 JUN 2014 | DOI: 10.1002/ejoc.201402372

      Thumbnail image of graphical abstract

      Quantum mechanical calculations together with statistical methods allowed the assignment of two new pentacyclic pyridoacridine alkaloids, ancorine A and cnemidine A. Cytotoxicity of the isolated compounds against PC3 prostate cancer cell line PC3 is reported.

    12. Decarboxylative Homocoupling

      Efficient and Reusable CuI/1,10-Phenanthroline-Catalyzed Oxidative Decarboxylative Homocoupling of Arylpropiolic Acids in Aqueous DMF (pages 4817–4822)

      De-Xian Liu, Fei-Long Li, Hong-Xi Li, Wei-Jie Gong, Jun Gao and Jian-Ping Lang

      Article first published online: 24 JUN 2014 | DOI: 10.1002/ejoc.201402416

      Thumbnail image of graphical abstract

      A CuI/1,10-phenanthroline system was employed to catalyze the oxidative decarboxylative homocoupling of arylpropiolic acids in aqueous DMF using air as an oxidant, producing 1,3-diynes in good to high yields. Such a catalytic system could be reused several times.

    13. Natural Product Synthesis

      A Unified Strategy for Kainoid Synthesis (pages 4823–4836)

      Masaya Fujii, Satoshi Yokoshima and Tohru Fukuyama

      Article first published online: 23 JUN 2014 | DOI: 10.1002/ejoc.201402452

      Thumbnail image of graphical abstract

      The syntheses of kainic acid, MFPA, and a cyclopropyl analog of kainic acid (CPKA) have been accomplished from a common intermediate. A unified strategy was used, featuring a Claisen–Ireland rearrangement to construct the contiguous stereogenic centers, and a palladium-catalyzed formation of the pyrrolidine ring with complete stereoselectivity.

    14. Nitrogen Heterocycles

      Hypervalent Iodine(III) Promoted Direct Synthesis of Imidazo[1,2-a]pyrimidines (pages 4837–4843)

      Guangyin Qian, Bingxin Liu, Qitao Tan, Siwen Zhang and Bin Xu

      Article first published online: 18 JUN 2014 | DOI: 10.1002/ejoc.201402456

      Thumbnail image of graphical abstract

      Imidazo[1,2-a]-type fused heterocycles are prevalent structural motifs in pharmaceutically and biologically active compounds. In this paper, an efficient and mild synthesis of imidazo[1,2-a]pyrimidine skeletons was developed from readily available pyrimidyl arylamines or enamines through a hypervalent iodine-promoted intramolecular C–H bond cycloamination reaction.

    15. Biomimetic Synthesis

      Biomimetic Synthesis of Functionalized γ-Resorcylates from Dioxinone Derivatives (pages 4844–4853)

      Peter S. Blencowe and Anthony G. M. Barrett

      Article first published online: 24 JUN 2014 | DOI: 10.1002/ejoc.201402473

      Thumbnail image of graphical abstract

      An efficient route to functionalized γ-resorcylate compounds is presented. The synthesis of substrates capable of an intramolecular acylation reaction was developed for this purpose.

    16. β-Keto Amide Synthesis

      Rapid and Structurally Diverse Synthesis of Multi-Substituted β-Keto Amide Derivatives Based on a Dioxinone Scaffold (pages 4854–4860)

      Shinichiro Fuse, Hayato Yoshida, Kazuya Oosumi and Takashi Takahashi

      Article first published online: 23 JUN 2014 | DOI: 10.1002/ejoc.201402478

      Thumbnail image of graphical abstract

      Multi-substituted β-keto amides were synthesized in a sequential four-component coupling process based on a dioxinone scaffold. The sequence consists of three steps: (1) nucleophilic addition of the scaffold to R1–CHO followed by a one-pot dehydration; (2) Pd-catalysed coupling of the scaffold with either R2–[B] or CO and R2–NH2; (3) nucleophilic addition of R3–NH2 to an in situ generated acyl ketene.

    17. Natural Products

      Total Synthesis of Blennolide Mycotoxins: Design, Synthetic Routes and Completion (pages 4861–4875)

      Anne C. Meister, Arantxa Encinas, Hülya Sahin, Emilie M. C. Singer, Carl F. Nising, Martin Nieger and Stefan Bräse

      Article first published online: 1 JUL 2014 | DOI: 10.1002/ejoc.201402083

      Thumbnail image of graphical abstract

      Two total syntheses of monomeric tetrahydroxanthone natural products are presented. The introduction of various functional groups by nucleophilic addition is extensively examined, and efforts towards the dimerization of these xanthones are reported.

    18. Synthetic Methods

      A Catalytic System for the Activation of Diorganozinc Reagents (pages 4876–4883)

      Thomas Werner, Matthias Bauer, Abdol Majid Riahi and Heiko Schramm

      Article first published online: 23 JUN 2014 | DOI: 10.1002/ejoc.201402138

      Thumbnail image of graphical abstract

      Sodium salts in combination with crown ethers efficiently activate diorganozinc. Catalytic amounts of sodium iodide and 15-crown-5 promote the conversion of various aldehydes. Efforts to apply EXAFS techniques to verify the mode of activation are described.

    19. Chiral Nitroxides

      Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization (pages 4884–4896)

      Marta Carbó López, Guy Royal, Christian Philouze, Pierre Y. Chavant and Véronique Blandin

      Article first published online: 24 JUN 2014 | DOI: 10.1002/ejoc.201402324

      Thumbnail image of graphical abstract

      New nitroxides based on the imidazolidinone skeleton have been studied as catalysts in aerobic oxidation reactions, and by cyclic voltammetry. Successful atroposelective desymmetrization of a diol was achieved with an enantiopure nitroxide.

    20. Organocatalysis

      Stereoselective Approach to 2,6-Disubstituted Piperidin-3-ol: Synthesis of (–)-Deoxoprosopinine and (+)-Deoxoprosophylline (pages 4897–4902)

      Vishwajeet Jha, Shruti Vandana Kauloorkar and Pradeep Kumar

      Article first published online: 23 JUN 2014 | DOI: 10.1002/ejoc.201402363

      Thumbnail image of graphical abstract

      A simple and highly efficient approach to an enantioenriched 2,6-disubstituted piperidin-3-ol skeleton is developed from an aldehyde as a starting material by using organocatalytic and asymmetric dihydroxylation as key steps. Its application to the total synthesis of (–)-deoxoprosopinine and (+)-deoxoprosophylline is also reported.

  7. Correction

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. You have free access to this content
      Synthesis of (S)- and (R)-Harmicine from Proline: An Approach Toward Tetrahydro-β-carbolines (page 4903)

      Christopher S. Lood and Ari M. P. Koskinen

      Article first published online: 2 JUL 2014 | DOI: 10.1002/ejoc.201402786

      This article corrects:

      Synthesis of (S)- and (R)-Harmicine from Proline: An Approach Toward Tetrahydro-β-carbolines

      Vol. 2014, Issue 11, 2357–2364, Article first published online: 12 FEB 2014

SEARCH

SEARCH BY CITATION