Faculty Profiles - SUGA Seiji

Papers - SUGA Seiji

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Electrogenerated Lewis Acid-Catalyzed Claisen Rearrangement of Allyl Aryl Ethers Reviewed

Yuta Niki, Koichi Mitsudo, Eisuke Sato, Seiji Suga

Organic Letters 2024.12

SNAr Hexafluoroisopropoxylation of Electron-rich Aryl Fluoride with a Catalytic Electrical Input Reviewed

Eisuke Sato, Tomohiro Nakahama, Koichi Mitsudo, Seiji Suga

Chemistry Letters 2024.10

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Oxford University Press (OUP)

Abstract

Anodic oxidation-promoted SNAr reactions of electron-rich aryl fluoride were developed. The anodic oxidation of 4-fluoroanisole in hexafluoroisopropyl alcohol (HFIP) with K2CO3 led to SNAr-type hexafluoroisopropoxylation, and the reaction was completed with a catalytic electrical input. The results of cyclic voltammetry suggest that the radical cation of 4-fluoroanisole, which would react with the alkoxide of HFIP, is generated. Electron transfer between the intermediate and the starting material constructs the catalytic cycle, and the elimination of fluoride from the Meisenheimer complex produces the desired compound.

DOI： 10.1093/chemle/upae196

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Electrocatalytic Hydrogenation of Pyridines and Other Nitrogen-Containing Aromatic Compounds Reviewed

Naoki Shida, Yugo Shimizu, Akizumi Yonezawa, Juri Harada, Yuka Furutani, Yusuke Muto, Ryo Kurihara, Junko N. Kondo, Eisuke Sato, Koichi Mitsudo, Seiji Suga, Shoji Iguchi, Kazuhide Kamiya, Mahito Atobe

Journal of the American Chemical Society 146 ( 44 ) 30212 - 30221 2024.10

Electrochemical synthesis of heterocyclic compounds via carbon–heteroatom bond formation: direct and indirect electrolysis Invited Reviewed

Yasuyuki Okumura, Eisuke Sato, Koichi Mitsudo, Seiji Suga

Chemistry Letters 53 ( 8 ) upae146 2024.7

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Oxford University Press (OUP)

Abstract

Electrochemical organic synthesis has attracted attention as an environmentally friendly method for constructing heterocyclic compounds via carbon–heteroatom bond formation. Herein, we describe the representative examples of electrochemical reactions to produce heterocycles and discuss them according to whether they involve direct or indirect electrolysis.

DOI： 10.1093/chemle/upae146

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Other Link： https://academic.oup.com/chemlett/article-pdf/53/8/upae146/58904624/upae146.pdf

Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor Invited Reviewed

Koichi Mitsudo, Atsushi Osaki, Haruka Inoue, Eisuke Sato, Naoki Shida, Mahito Atobe, Seiji Suga

Beilstein Journal of Organic Chemistry 20 1560 - 1571 2024.7

Language：English Publishing type：Research paper (scientific journal) Publisher：Beilstein Institut

An electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines using a proton-exchange membrane (PEM) reactor was developed. Cyanoarenes were then reduced to the corresponding benzylamines at room temperature in the presence of ethyl phosphate. The reduction of nitroarenes proceeded at room temperature, and a variety of anilines were obtained. The quinoline reduction was efficiently promoted by adding a catalytic amount of p-toluenesulfonic acid (PTSA) or pyridinium p-toluenesulfonate (PPTS). Pyridine was also reduced to piperidine in the presence of PTSA.

DOI： 10.3762/bjoc.20.139

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Other Link： https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-20-139.pdf

Sequential Paired Electrochemical Transformation of Styrene Oxide via Anodic Meinwald Rearrangement and Cathodic Nitromethylation in an Electrochemical Flow Reactor with Catalytic Electrical Input

Eisuke Sato, Kanon Nagamine, Chika Sasaki, Shumpei Kunimoto, Koichi Mitsudo, Seiji Suga

Synthesis 56 ( 16 ) 2507 - 2512 2024.4

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Georg Thieme Verlag KG

Abstract

Paired electrosynthesis, which utilize both anodic and cathodic events in electrolysis, enables attractive transformations with higher current efficiency than conventional electrosynthesis. The electrochemical flow technique has been widely employed to ensure stable reaction conditions and mitigate issues stemming from mass transfer. In this study, the electrochemical Meinwald rearrangement of styrene oxides was investigated, yielding aldehydes as intermediates, followed by the nitromethylation of aldehydes to produce β-nitro alcohols. These reactions were achieved with catalytic electrical input, enabling the conversion of various styrene oxides into the corresponding β-nitro alcohols.

DOI： 10.1055/a-2309-6737

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[1,2]-Retro-Brook rearrangement induced by electrochemical reduction of silyl enolates

Ban Kinoshita, Saki Maejima, Yuta Niki, Koichi Mitsudo, Seiji Suga, Hideki Yorimitsu

Bulletin of the Chemical Society of Japan 97 ( 4 ) uoae038 2024.3

Language：English Publishing type：Research paper (scientific journal) Publisher：Oxford University Press (OUP)

Abstract

Electrochemical reduction of the trimethylsilyl enolates of alkyl aryl ketones induces retro-Brook rearrangement to provide 1-aryl-1-trimethylsilylalkan-1-ols. The transformation proceeds through a sequence of 1) single-electron reduction of the silyl enolate, 2) protonation with a phenol, 3) another single-electron reduction to form a siloxy-substituted benzylic anion, and 4) the pivotal retro-Brook rearrangement.

DOI： 10.1093/bulcsj/uoae038

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Other Link： https://academic.oup.com/bcsj/article-pdf/97/4/uoae038/57322484/uoae038.pdf

Terrein Exhibits Anti-tumor Activity by Suppressing Angiogenin Expression in Malignant Melanoma Cells. Reviewed International journal

Taira Hirose, Yuki Kunisada, Koichi Kadoya, Hiroki Mandai, Yumi Sakamoto, Kyoichi Obata, Kisho Ono, Hiroaki Takakura, Kazuhiro Omori, Shogo Takashiba, Seiji Suga, Soichiro Ibaragi

Cancer genomics & proteomics 21 ( 5 ) 464 - 473 2024

Language：English Publishing type：Research paper (scientific journal)

BACKGROUND/AIM: Malignant melanoma is a tumor with a poor prognosis that can metastasize distally at an early stage. Terrein, a metabolite produced by Aspergillus terreus, suppresses the expression of angiogenin, an angiogenic factor. However, the pharmacological effects of natural terrein have not been elucidated, because only a small amount of terrein can be extracted from large fungal cultures. In this study, we investigated the antineoplastic effects of terrein on human malignant melanoma cells and its underlying mechanisms. MATERIALS AND METHODS: Human malignant melanoma cell lines were cultured in the presence of terrein and analyzed. Angiogenin production was evaluated using ELISA. Ribosome biosynthesis was evaluated using silver staining of the nucleolar organizer region. Intracellular signaling pathways were analyzed using western blotting. Malignant melanoma cells were transplanted subcutaneously into the backs of nude mice. The tumors were removed at 5 weeks and analyzed histopathologically. RESULTS: Terrein inhibited angiogenin expression, proliferation, migration, invasion, and ribosome biosynthesis in malignant melanoma cells. Terrein was shown to inhibit tumor growth and angiogenesis in animal models. CONCLUSION: This study demonstrated that terrein has anti-tumor effects against malignant melanoma. Furthermore, chemically synthesized non-natural terrein can be mass-produced and serve as a novel potential anti-tumor drug candidate.

DOI： 10.21873/cgp.20464

PubMed

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Alkynylation of Aldehydes Initiated by Cathodic Reduction Invited Reviewed

Eisuke Sato, Mayu Fujii, Koichi Mitsudo, Seiji Suga

ChemElectroChem 11 ( 1 ) 2023.12

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Wiley

Abstract

Alkynylation of aldehydes initiated by cathodic reduction was performed. The cathodic alkynylation required only a semi‐catalytic amount of electricity to consume the starting material completely. Cyclic voltammetry and some control experiments suggest that the electron‐generated base derived from the cathodic reduction of benzaldehyde promotes alkynylation.

DOI： 10.1002/celc.202300499

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Electrochemical Synthesis of Dibenzothiophene S,S-Dioxides from Biaryl Sulfonyl Hydrazides Invited Reviewed

Yasuyuki OKUMURA, Eisuke SATO, Koichi MITSUDO, Seiji SUGA

Electrochemistry 91 ( 11 ) 112007 2023.11

Cathodic N–O Bond Cleavage of N-Alkoxy Amide Invited Reviewed

Eisuke SATO, Sayaka OGITA, Koichi MITSUDO, Seiji SUGA

Electrochemistry 91 ( 11 ) 112005 2023.11

Electrochemical Coupling Reactions Using Non‐Transition Metal Mediators: Recent Advances Invited Reviewed

Koichi Mitsudo, Yasuyuki Okumura, Eisuke Sato, Seiji Suga

European Journal of Organic Chemistry 26 ( 47 ) e202300835 2023.11

Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Wiley

Abstract

Indirect electrolysis method using appropriate mediators enables numerous chemical reactions. The general principles of mediators were described herein with a particular focus on non‐transition metal mediators. Recent representative examples of bond formation reactions by indirect electrolysis are summarized and discussed here.

DOI： 10.1002/ejoc.202300835

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Anodic Dehydrogenative Aromatization of Tetrahydrocarbazoles Leading to Carbazoles Reviewed

Eisuke Sato, Ayaka Yukiue, Koichi Mitsudo, Seiji Suga

Organic Letters 25 ( 28 ) 5339 - 5344 2023.7

Electrochemical Synthesis of Sultone Derivatives via Dehydrogenative C-O Bond Formation. Reviewed International journal

Koichi Mitsudo, Yasuyuki Okumura, Kotaro Yohena, Yuji Kurimoto, Eisuke Sato, Seiji Suga

Organic letters 25 ( 19 ) 3476 - 3481 2023.5

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal)

Electrochemical dehydrogenative C-O bond formation for the synthesis of sultones was achieved. In the presence of K2CO3 and H2O, constant current electrolysis of [1,1'-biphenyl]-2-sulfonyl chloride afforded an aryl-fused sultone quantitatively. Under the optimized conditions, a variety of sultone derivatives were obtained. Control experiments suggest that the electrochemical oxidation of the sulfonates generated in situ would afford sulfo radical intermediates.

DOI： 10.1021/acs.orglett.3c01062

PubMed

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The Fungal Metabolite (+)-Terrein Abrogates Inflammatory Bone Resorption via the Suppression of TNF-α Production in a Ligature-Induced Periodontitis Mouse Model Reviewed

Hidefumi Sako, Kazuhiro Omori, Masaaki Nakayama, Hiroki Mandai, Hidetaka Ideguchi, Saki Yoshimura-Nakagawa, Kyosuke Sakaida, Chiaki Nagata-Kamei, Hiroya Kobayashi, Satoki Ishii, Mitsuaki Ono, Soichiro Ibaragi, Tadashi Yamamoto, Seiji Suga, Shogo Takashiba

Journal of Fungi 9 ( 3 ) 314 - 314 2023.3

Language：English Publishing type：Research paper (scientific journal) Publisher：MDPI AG

Current periodontal treatment focuses on the mechanical removal of the source of infection, such as bacteria and their products, and there is no approach to control the host inflammatory response that leads to tissue destruction. In order to control periodontal inflammation, we have previously reported the optimization of (+)-terrein synthesis methods and the inhibitory effect of (+)-terrein on osteoclast differentiation in vitro. However, the pharmacological effect of (+)-terrein in vivo in the periodontitis model is still unknown. In this study, we investigated the effect of synthetic (+)-terrein on inflammatory bone resorption using a ligature-induced periodontitis mouse model. Synthetic (+)-terrein (30 mg/kg) was administered intraperitoneally twice a week to the mouse periodontitis model. The control group was treated with phosphate buffer. One to two weeks after the induction of periodontitis, the periodontal tissues were harvested for radiological evaluation (micro-CT), histological evaluation (HE staining and TRAP staining), and the evaluation of inflammatory cytokine production in the periodontal tissues and serum (quantitative reverse-transcription PCR, ELISA). The synthetic (+)-terrein-treated group suppressed alveolar bone resorption and the number of osteoclasts in the periodontal tissues compared to the control group (p < 0.05). In addition, synthetic (+)-terrein significantly suppressed both mRNA expression of TNF-α in the periodontal tissues and the serum concentration of TNF-α (both p < 0.05). In conclusion, we have demonstrated that synthetic (+)-terrein abrogates alveolar bone resorption via the suppression of TNF-α production and osteoclast differentiation in vivo. Therefore, we could expect potential clinical effects when using (+)-terrein on inflammatory bone resorption, including periodontitis.

DOI： 10.3390/jof9030314

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Electrochemical Cross-Coupling Reactions between Arylboronic Esters and Aryllithiums Using NaBr as a Halogen Mediator Invited Reviewed

Koichi Mitsudo, Seiji Suga, Keisuke Shigemori, Taro Shibata, Hiroki Mandai, Eisuke Sato

Synthesis 55 ( 18 ) 2999 - 3004 2023.2

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Georg Thieme Verlag KG

Abstract

An electrochemical cross-coupling reaction between arylboronic esters and aryllithiums was developed. The presence of Br– in the electrolyte was found to be essential for the reaction. NaBr was chosen as the electrolyte for its inexpensiveness and abundance, and also acted as a halogen mediator. The reaction proceeded under mild conditions to afford biaryls.

DOI： 10.1055/a-2034-9821

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Electrochemical Carbon-Ferrier Rearrangement Using a Microflow Reactor and Machine Learning-Assisted Exploration of Suitable Conditions Reviewed

Eisuke Sato, Gaku Tachiwaki, Mayu Fujii, Koichi Mitsudo, Takashi Washio, Shinobu Takizawa, Seiji Suga

Organic Process Research & Development 28 ( 5 ) 1422 - 1429 2023.1

Electrochemical Synthesis of Dibenzothiophenes via Intramolecular C–S Cyclization with a Halogen Mediator Reviewed

Koichi Mitsudo, Yuri Tachibana, Eisuke Sato, Seiji Suga

Organic Letters 24 ( 46 ) 8547 - 8552 2022.11

A Facile Access to Spirooxindoles by Halogen-mediated Electrochemical Semi-pinacol Rearrangement Reviewed

Eisuke Sato, Sae Kangawa, Koichi Mitsudo, Seiji Suga

Chemistry Letters 51 ( 11 ) 1067 - 1069 2022.11

Electrochemical hydrogenation of enones using a proton-exchange membrane reactor: selectivity and utility Invited Reviewed

Koichi Mitsudo, Haruka Inoue, Yuta Niki, Eisuke Sato, Seiji Suga

Beilstein Journal of Organic Chemistry 18 1055 - 1061 2022.8

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Beilstein Institut

Electrochemical hydrogenation of enones using a proton-exchange membrane reactor is described. The reduction of enones proceeded smoothly under mild conditions to afford ketones or alcohols. The reaction occurred chemoselectively with the use of different cathode catalysts (Pd/C or Ir/C).

DOI： 10.3762/bjoc.18.107

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Other Link： https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-18-107.pdf

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