Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
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Volume 74, Issue 2
Displaying 1-9 of 9 articles from this issue
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Preface
Reviews and Accounts
  • Unified Total Synthesis of Tryptophan-based Dimeric Diketopiperazine Alkaloids
    Hayato Ishikawa
    2016 Volume 74 Issue 2 Pages 104-116
    Published: February 01, 2016
    Released on J-STAGE: March 22, 2016
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.74.104
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    A concise synthesis of WIN 64821 (1), eurocristatine (2), 15,15’-bis-epi-eurocristatine (3), ditryptophenaline (4), ditryptoleucine A (6), WIN 64745 (7), cristatumin C (8), asperdimin (9), naseseazine A (10), and naseseazine B (11) is detailed based on a unique bioinspired dimerization reaction of tryptophan derivatives in aqueous acidic solution and one-pot procedure for construction of diketopiperazine rings. Total yields of these alkaloid syntheses were from 10% up to 27%. In addition, 1’-(2-phenylethylene)-ditryptophenaline (5) was synthesized using three one-pot operations. The studies detailed herein provided synthesized natural products for inhibitory activities of ubiquitin-specific protease 7 (USP7) and foam cell formation in macrophages.
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  • Palladium-catalyzed Cross-coupling Reaction of Indolylborates and its Application for the Syntheses of Indole Alkaloids
    Takumi Abe, Minoru Ishikura
    2016 Volume 74 Issue 2 Pages 117-129
    Published: February 01, 2016
    Released on J-STAGE: March 22, 2016
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.74.117
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    In our continuing study of the reactivity and synthetic application of indolylborate as a versatile synthetic intermediate, we found that the use of indolylborate in palladium-catalyzed cross-coupling reaction is highly effective for the synthesis of indole derivatives. The present account deals with the results concerning a novel approach to indole alkaloids based on the use of the palladium-catalyzed cross-coupling. Dimeric indole alkaloid, yuechuke, was synthesized through the palladium-catalyzed carbonylative cross-coupling reaction. Pyridocarbazole alkaloids (ellipticine, olivacine, and their related alkaloids), and indolophenanthridine alkaloid (calothrixins A and B) were obtained by the use of cyclization/cross-coupling domino reaction. In addition, (CuOTf)2·toluene complex was demonstrated to catalyze 6π-electrocyclization of hexatrienes, leading to pyrido [4,3-b] carbazoles.
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  • Synthesis of Nitroarenes Using Three-Component Ring Transformation
    Haruyasu Asahara, Song Thi Le, Nagatoshi Nishiwaki
    2016 Volume 74 Issue 2 Pages 130-140
    Published: February 01, 2016
    Released on J-STAGE: March 22, 2016
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.74.130
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    1-Methyl-3,5-dinitropyridone serves as an excellent substrate for the nucleophilic-type three-component ring transformation (TCRT). The reaction of dinitropyridone with aromatic ketones in the presence of ammonium acetate afforded 2-arylated 5-nitropyridines. In the TCRTs using cycloalkanones and α,β-unsaturated ketones, nitrated cycloalka[b]pyridines and alkenyl/alkynylpyridines were obtained, respectively. This protocol was also applicable to reactive aldehydes, which affords 3-substituted 5-nitropyridines. On the other hand, aliphatic ketones having two kinds of α-protons underwent a different type ring transformation leading to 2,6-disubstituted 4-nitroanilines. It was possible to use a combination of amine and acetic acid, by which N,N,2,6-tetrasubstituted nitroanilines were synthesized. This TCRT will be an efficient method for the synthesis of compounds possessing both an electron-donating and electron-withdrawing groups, which are useful for developing new functional materials.
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  • Synthesis and Properties of 2’,4’-Bridged Nucleic Acids Containing Multiple Heteroatoms in the Bridges
    Yoshiyuki Hari, Satoshi Obika
    2016 Volume 74 Issue 2 Pages 141-153
    Published: February 01, 2016
    Released on J-STAGE: March 22, 2016
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.74.141
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    Nucleic acids bridged between 2’- and 4’-positions are attracting much attention because the oligonucleotides bearing these derivatives generally increase in the binding affinity with single-stranded RNA and have an increased resistance against nuclease. It is found that their properties are greatly affected by size and composition of the bridge. In particular, introduction of heteroatom into the bridge unit is considered to give an influence on network of surrounding water molecules in formation of nucleic acid complex. Therefore, it would be meaningful to investigate and understand the properties of various 2’,4’-bridged nucleic acids. Under such a background, this account focuses on 2’,4’-bridged nucleic acids containing multiple heteroatoms in the bridge structures, with five-, six- and seven-membered bridges, have recently been reported by us, and the synthesis, duplex-forming ability with single-stranded nucleic acid and nuclease resistance of their modified oligonucleotides are mainly described.
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  • Development of Trifluoroethoxy Substituted Phthalocyanines and Subphthalocyanines and their Applications
    Satoru Mori, Norio Shibata
    2016 Volume 74 Issue 2 Pages 154-166
    Published: February 01, 2016
    Released on J-STAGE: March 22, 2016
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.74.154
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    Phthalocyanines and subphthalocyanines have been considerably researched in both academia and industry for the development of advanced materials such as photosensitizers for organic solar cells, anti-cancer agents for photodynamic therapy, electrochromic devices and among others. For the last decade, we have been interested in phthalocyanines having fluorine(s) at their peripheral positions, due to their specific properties induced by fluorine atoms; in particular, trifluoroethoxy-coated phthalocyanines. This review introduces the synthesis and application of trifluoroethoxy peri- substituted phthalocyanines and subphthalocyanines reported by our research group. The utilities and advantages induced by trifluoroethoxy group onto phthalocyanines and subphthalocyanines are discussed comparing to the well-studied analogues of non-substituted or tert-butyl substituted ones.
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