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  1. Article ; Online: Directing carboxylic acid dehydrogenation.

    Iwabuchi, Yoshiharu

    Science (New York, N.Y.)

    2021  Volume 374, Issue 6572, Page(s) 1199

    Abstract: A palladium ligand can activate carbon-hydrogen bonds yet avoid product olefin reactions. ...

    Abstract A palladium ligand can activate carbon-hydrogen bonds yet avoid product olefin reactions.
    MeSH term(s) Carboxylic Acids
    Chemical Substances Carboxylic Acids
    Language English
    Publishing date 2021-12-02
    Publishing country United States
    Document type Journal Article ; Comment
    ZDB-ID 128410-1
    ISSN 1095-9203 ; 0036-8075
    ISSN (online) 1095-9203
    ISSN 0036-8075
    DOI 10.1126/science.abm4457
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: C-H Alkylation of Cubanes via Catalytic Generation of Cubyl Radicals.

    Hosaka, Masaki / Nagasawa, Shota / Iwabuchi, Yoshiharu

    Organic letters

    2024  Volume 26, Issue 3, Page(s) 658–663

    Abstract: A catalytic method for the C-H alkylation of cubanes is described. Some hydrogen atom transfer catalysts enable the direct abstraction of a hydrogen atom from the C-H bond of cubanes, followed by conjugate addition of the generated cubyl radicals to ... ...

    Abstract A catalytic method for the C-H alkylation of cubanes is described. Some hydrogen atom transfer catalysts enable the direct abstraction of a hydrogen atom from the C-H bond of cubanes, followed by conjugate addition of the generated cubyl radicals to electron-deficient alkenes. Synthetic applications of the functionalization method developed are also described.
    Language English
    Publishing date 2024-01-18
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.3c04019
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Controlled Aerobic Oxidative Dimerization of Hydroxystilbenoids by Chromium Catalysis.

    Nagasawa, Shota / Itagaki, Yudai / Sasano, Yusuke / Iwabuchi, Yoshiharu

    Organic letters

    2024  

    Abstract: Aerobic oxidative dimerization of hydroxystilbenoids is described. A Cr-salen complex catalyzed the dimerization of hydroxystilbenoids in 1,1,1,3,3,3-hexafluoroisopropanol to form compounds comprising a natural product-like scaffold (quadrangularin) or ... ...

    Abstract Aerobic oxidative dimerization of hydroxystilbenoids is described. A Cr-salen complex catalyzed the dimerization of hydroxystilbenoids in 1,1,1,3,3,3-hexafluoroisopropanol to form compounds comprising a natural product-like scaffold (quadrangularin) or its precursor depending on the aromatic substituents. The addition of a catalytic amount of scandium triflate [Sc(OTf)
    Language English
    Publishing date 2024-05-10
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.4c00839
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article: Azetidine synthesis by La(OTf)

    Kuriyama, Yuse / Sasano, Yusuke / Iwabuchi, Yoshiharu

    Frontiers in chemistry

    2023  Volume 11, Page(s) 1251299

    Abstract: Azetidine is a prevalent structural motif found in various biologically active compounds. In this research paper, we report La(OTf) ...

    Abstract Azetidine is a prevalent structural motif found in various biologically active compounds. In this research paper, we report La(OTf)
    Language English
    Publishing date 2023-09-19
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2711776-5
    ISSN 2296-2646
    ISSN 2296-2646
    DOI 10.3389/fchem.2023.1251299
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Comprehensive Structural and Electronic Properties of 2-Azaadamantane

    Nishijima, Masaki / Sasano, Yusuke / Iwabuchi, Yoshiharu / Araki, Yasuyuki

    ACS omega

    2023  Volume 8, Issue 51, Page(s) 49067–49072

    Abstract: Herein, a comprehensive kinetic study is performed to compare the catalytic efficiency of 2- ... ...

    Abstract Herein, a comprehensive kinetic study is performed to compare the catalytic efficiency of 2-azaadamantane
    Language English
    Publishing date 2023-12-14
    Publishing country United States
    Document type Journal Article
    ISSN 2470-1343
    ISSN (online) 2470-1343
    DOI 10.1021/acsomega.3c06902
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: Biological Evaluation of Isosteric Applicability of 1,3-Substituted Cuneanes as m-Substituted Benzenes Enabled by Selective Isomerization of 1,4-Substituted Cubanes.

    Fujiwara, Kan / Nagasawa, Shota / Maeyama, Ryusei / Segawa, Ryosuke / Hirasawa, Noriyasu / Hirokawa, Takatsugu / Iwabuchi, Yoshiharu

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2024  Volume 30, Issue 11, Page(s) e202303548

    Abstract: We herein evaluate a biological applicability of 1,3-substituted cuneanes as an isostere of m-substituted benzenes based on its structural similarity. An investigation of a method to obtain 1,3-substituted cuneanes by selective isomerization of 1,4- ... ...

    Abstract We herein evaluate a biological applicability of 1,3-substituted cuneanes as an isostere of m-substituted benzenes based on its structural similarity. An investigation of a method to obtain 1,3-substituted cuneanes by selective isomerization of 1,4-substituted cubanes enables this attempt by giving a key synthetic step to obtain a cuneane analogs of pharmaceuticals having m-substituted benzene moiety. Biological evaluation of the synthesized analogs and in silico study of the obtained result revealed a potential usage of cuneane skeleton in medicinal chemistry.
    MeSH term(s) Benzene/chemistry ; Isomerism ; Benzene Derivatives/chemistry
    Chemical Substances Benzene (J64922108F) ; Benzene Derivatives
    Language English
    Publishing date 2024-01-11
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202303548
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Mono-Carbonyl Curcumin Analogs for Cancer Therapy.

    MaruYama, Takashi / Yamakoshi, Hiroyuki / Iwabuchi, Yoshiharu / Shibata, Hiroyuki

    Biological & pharmaceutical bulletin

    2023  Volume 46, Issue 6, Page(s) 756–763

    Abstract: Curcumin has long been recognized for its anti-inflammatory properties. An antitumor effect has been recently reported in curcumin and clinical trials are being conducted. However, a large amount of required intake to obtain the antitumor effect of ... ...

    Abstract Curcumin has long been recognized for its anti-inflammatory properties. An antitumor effect has been recently reported in curcumin and clinical trials are being conducted. However, a large amount of required intake to obtain the antitumor effect of curcumin has been regarded as a problem. Therefore, curcumin analogs have been created by many researchers to enhance the effects of curcumin. We have synthesized >50 curcumin analogs and revealed greater growth suppression of various tumor cells with mono-carbonyl analogs than curcumin. Mechanistically, mono-carbonyl analogs inhibited transcriptional activity (e.g., nuclear factor kappa B, signal transducer, and activator of transcription 3) or activated caspase-3. Additionally, mono-carbonyl analogs of curcumin control tumor cell metabolism. Herein, we summarize the current knowledge about mono-carbonyl curcumin analogs and discuss their potential clinical applications.
    MeSH term(s) Humans ; Curcumin/pharmacology ; Curcumin/therapeutic use ; Neoplasms/drug therapy ; Anti-Inflammatory Agents/pharmacology ; NF-kappa B/metabolism ; Cell Line, Tumor
    Chemical Substances Curcumin (IT942ZTH98) ; Anti-Inflammatory Agents ; NF-kappa B
    Language English
    Publishing date 2023-05-31
    Publishing country Japan
    Document type Journal Article
    ZDB-ID 1150271-x
    ISSN 1347-5215 ; 0918-6158
    ISSN (online) 1347-5215
    ISSN 0918-6158
    DOI 10.1248/bpb.b23-00103
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  8. Article ; Online: Enantiocontrolled Access to an Intermediate for Highly Functionalized Clovane-Type Terpenoids: Formal Synthesis of Rumphellclovane E.

    Ninomiya, Daigo / Nagasawa, Shota / Iwabuchi, Yoshiharu

    Organic letters

    2022  Volume 24, Issue 41, Page(s) 7572–7576

    Abstract: We describe an enantiocontrolled route to a versatile intermediate for the synthesis of highly functionalized clovane-type terpenoids. The synthetic route commenced with ( ... R ... )-carvone, a commercially available and enantioenriched building block, and ...

    Abstract We describe an enantiocontrolled route to a versatile intermediate for the synthesis of highly functionalized clovane-type terpenoids. The synthetic route commenced with (R)-carvone, a commercially available and enantioenriched building block, and an oxygenative strategy was used to concisely access a clovane scaffold. One example of the versatility of the obtained intermediate was the formal synthesis of rumphellclovane E.
    MeSH term(s) Terpenes ; Stereoisomerism
    Chemical Substances Terpenes
    Language English
    Publishing date 2022-10-11
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.2c02960
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  9. Article: ortho-C–H Acetoxylation of Cubane Enabling Access to Cubane Analogues of Pharmaceutically Relevant Scaffolds

    Nagasawa, Shota / Hosaka, Masaki / Iwabuchi, Yoshiharu

    Organic letters. 2021 Oct. 21, v. 23, no. 22

    2021  

    Abstract: A novel method of introducing an oxygen functionality into a cubane core was developed using a transition-metal-catalyzed directed acetoxylation methodology via C–H activation. The obtained compounds were derivatized into cubane analogues of ... ...

    Abstract A novel method of introducing an oxygen functionality into a cubane core was developed using a transition-metal-catalyzed directed acetoxylation methodology via C–H activation. The obtained compounds were derivatized into cubane analogues of pharmaceutically relevant structural motifs, namely, acetylsalicylic acid and coumarin motifs, which could potentially act as bioisosteres of these scaffolds.
    Keywords aspirin ; carbon-hydrogen bond activation ; coumarin ; oxygen
    Language English
    Dates of publication 2021-1021
    Size p. 8717-8721.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.1c03144
    Database NAL-Catalogue (AGRICOLA)

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  10. Article: Chromium–Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

    Nagasawa, Shota / Fujiki, Shogo / Sasano, Yusuke / Iwabuchi, Yoshiharu

    Journal of organic chemistry. 2021 Apr. 23, v. 86, no. 9

    2021  

    Abstract: We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium–salen (Cr–salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various ... ...

    Abstract We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium–salen (Cr–salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.
    Keywords catalytic activity ; cooperatives ; couplings ; free radicals ; journals ; organic chemistry ; phenol
    Language English
    Dates of publication 2021-0423
    Size p. 6952-6968.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c00438
    Database NAL-Catalogue (AGRICOLA)

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