Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
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Volume 72, Issue 6
Displaying 1-13 of 13 articles from this issue
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Preface
Reviews and Accounts
  • Reactivity of Propargylic Amines in the Presence of Transition Metals
    Tsuyuka Sugiishi, Hiroyuki Nakamura
    2014 Volume 72 Issue 6 Pages 654-665
    Published: June 01, 2014
    Released on J-STAGE: July 16, 2014
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.72.654
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    N,N-Dialkyl-substituted propargylic amines undergo various transformations in the presence of transition-metal catalysts: The hydride-transfer reaction in the presence of palladium catalysts to afford the corresponding allenes, the fragment-exchange reaction with amines or acetylenes in the presence of copper(I) catalysts through C(sp)-C(sp3) bond cleavage, and the redox cross-dehydrogenative coupling in the presence of zinc(II) catalysts to afford N-tethered 1,6-enynes. In all the above cases, the generation of iminium intermediates, which would be assisted by a lone pair on the nitrogen atom of the propargylic amines, is essential for further transformations.
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  • Effective Synthetic Reactions using Highly Reactive Michael Acceptors, Ethenetricarboxylates
    Shoko Yamazaki
    2014 Volume 72 Issue 6 Pages 666-679
    Published: June 01, 2014
    Released on J-STAGE: July 16, 2014
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.72.666
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    The development of new efficient bond-forming reactions is important in synthetic organic chemistry. Recent developments concerning the synthetic methods utilizing highly electrophilic Michael acceptors, ethenetricarboxylates are described. Ethenetricarboxylate is a member of methylenemalonates and more reactive than alkylidenemalonates by the electron-withdrawing effect of 2-ester group. In particular, Lewis acids promote the reactions of ethenetricarboxylate derivatives efficiently. Various nucleophiles could undergo conjugate additions and the further bond-forming reactions. The high functionalization of the products may be useful for further elaboration.
    This paper describes catalytic Friedel-Crafts/Michael addition reactions of indoles, conjugate addition of amines, and various cycloadditions with compounds such as propargyl amines/alcohols, aminobenzaldehydes, and allenes in the presence of Lewis acid to give nitrogen and oxygen-containing heterocyclic and carbocyclic compounds. One-pot reactions with compounds such as aminoalcohol and Huisgen zwitterion in the absence of Lewis acids lead to various heterocyclic compounds. Lewis acid-promoted intramolecular cyclization reactions of functionalized ethenetricarboxylate derivatives has also been described.
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  • Synthesis of Fluorinated Heterocycles Designed to Deliver the Modified Bioactive Behavior: Synthetic Use of Ethyl Bromodifluoroacetate, Ethyl Dibromofluoroacetate and Fluorine Containing Vinylsilanes
    Atsushi Tarui, Kazuyuki Sato, Masaaki Omote, Akira Ando
    2014 Volume 72 Issue 6 Pages 680-691
    Published: June 01, 2014
    Released on J-STAGE: July 16, 2014
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.72.680
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    The incorporation of fluorine into heterocyclic compounds has a great impact on the electron distributional profile to change the character of permanent dipole moment, pKa constant of heteroatoms and hydrogen bonding pattern. The technique has been often used for drug discovery process to control pharmacological properties of the parent compounds. Fluorinated β-lactams, aziridines and α,β-unsaturated-δ-lactones are considered as important motifs possible to modify their enzyme inhibition activity. Fluorinated quinolines are understood as privileged structure of antibacterial, antimalarial and anti-inflammatory medicines. These fluorinated heterocycles are now becoming the topics of recent organic synthesis and medicinal chemistry, while the synthetic approaches remain challenging. In this paper, we would like to introduce our recent progress to exploit such approaches for the fluorinated bioactive heterocycles by the use of ethyl bromodifluoroacetate, ethyl dibromofluoroacetate and fluorine-containing vinylsilanes.
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  • Creation of Three-Dimensional Nanostructures with Anthracene Shells
    Keita Hagiwara, Michito Yoshizawa
    2014 Volume 72 Issue 6 Pages 692-701
    Published: June 01, 2014
    Released on J-STAGE: July 16, 2014
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.72.692
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    Anthracene is one of the planar polyaromatic compounds with intriguing reactivities and properties so that the unit has been widely used to construct functional molecules and molecular assemblies through covalent and non-covalent linkages. The intrinsic features of the embedded anthracenes often interact to engender unique chemical behaviors and physical properties in multiple anthracene assemblies. This review article focuses on the preparation of novel three-dimensional nanostructures with tube, bowl, and capsule shapes, providing well-defined cavities encircled by anthracene shells. Interestingly, most of them showed unusual structural, emissive, and/or host properties.
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  • Target-guided Synthesis: Medicinal Chemistry Strategy to Allow Target Enzymes Themselves to Synthesize their Own Inhibitors
    Yukihiro Itoh, Naoki Miyata, Takayoshi Suzuki
    2014 Volume 72 Issue 6 Pages 702-716
    Published: June 01, 2014
    Released on J-STAGE: July 16, 2014
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.72.702
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    Target-guided synthesis (TGS) is the method to allow target enzymes to synthesize their own inhibitors. The inhibitors identified by TGS are expected to show strong activity and high target-selectivity because they are synthesized by a specific reaction and/or in specific pockets of a target enzyme. Therefore, this approach would be useful for discovering novel selective enzyme inhibitors. Thus far, we found various enzyme inhibitors by means of TGS, i.e. (i) histone deacetylase (HDAC), human sirtuin (SIRT) and lysine-specific demethylase 1 (LSD1) inhibitors designed based on the enzymatic reaction mechanisms, (ii) LSD1 inactivators designed based on a direct target-drug delivery system and (iii) an HDAC8 inhibitor identified by in situ click chemistry utilizing an HDAC8/copper complex as a template. Here we present the design, synthesis, biological evaluation and inhibition mechanism analysis of these inhibitors.
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  • Diversity in Furanoeremophilane Composition Produced by Ligularia Species (Asteraceae) in the Hengduan Mountains Area of China
    Chiaki Kuroda, Ryo Hanai, Motoo Tori, Yasuko Okamoto, Yoshinori Saito, ...
    2014 Volume 72 Issue 6 Pages 717-725
    Published: June 01, 2014
    Released on J-STAGE: July 16, 2014
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.72.717
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    A series of our studies on the chemical and genetic diversity of Ligularia species in the Hengduan Mountains area of China is reviewed. Diversities were detected in various species in terpenoid compositions and DNA sequences of the ITS region. Furanoeremophilanes were isolated from many species together with eremophilan-8-ones. Samples of some species such as L. virgaurea were grouped into two or more chemotypes, while L. cymbulifera and L. cyathiceps were uniform. Complex diversity was found in L. kanaitzensis. A hypothesis that the production of furanoeremophilanes is ecologically advantageous was proposed. Production of terpenoids in L. duciformis and related species were suggested to be acquired by hybridization which may be one of the major pathways of the evolution of Ligularia. Some taxonomically close species, such as L. lamarum and L. subspicata, were indistinguishable in both the root chemicals and the ITS sequences.
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