Faculty Profiles - SUGA Seiji

Papers - SUGA Seiji

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Electro-oxidative Trimerization of 1,2-Dimethoxybenzene: Reductive Workup Strategy and Alternating Current Electrolysis to Peel off the Precipitated Radical Cation Ion Pair Reviewed

Eisuke Sato, Yuta Niki, Koichi Mitsudo, Seiji Suga

Chemistry Letters 51 ( 6 ) 629 - 632 2022.6

Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis Reviewed

Eisuke Sato, Mayu Fujii, Hiroki Tanaka, Koichi Mitsudo, Masaru Kondo, Shinobu Takizawa, Hiroaki Sasai, Takeshi Washio, Kazunori Ishikawa, Seiji Suga

The Journal of Organic Chemistry 86 ( 22 ) 16035 - 16044 2021.8

The Fungal Metabolite (+)-Terrein Abrogates Ovariectomy-Induced Bone Loss and Receptor Activator of Nuclear Factor-κB Ligand–Induced Osteoclastogenesis by Suppressing Protein Kinase-C α/βII Phosphorylation Reviewed

Kyosuke Sakaida, Kazuhiro Omori, Masaaki Nakayama, Hiroki Mandai, Saki Nakagawa, Hidefumi Sako, Chiaki Kamei, Satoshi Yamamoto, Hiroya Kobayashi, Satoki Ishii, Mitsuaki Ono, Soichiro Ibaragi, Keisuke Yamashiro, Tadashi Yamamoto, Seiji Suga, Shogo Takashiba

Frontiers in Pharmacology 12 674366 2021.6

Language：English Publishing type：Research paper (scientific journal) Publisher：Frontiers Media SA

Osteoporosis is a common disease characterized by a systemic impairment of bone mass and microarchitecture that results in fragility fractures. Severe bone loss due to osteoporosis triggers pathological fractures and consequently decreases the daily life activity and quality of life. Therefore, prevention of osteoporosis has become an important issue to be addressed. We have reported that the fungal secondary metabolite (+)-terrein (TER), a natural compound derived from Aspergillus terreus, has shown receptor activator of nuclear factor-κB ligand (RANKL)–induced osteoclast differentiation by suppressing nuclear factor of activated T-cell 1 (NFATc1) expression, a master regulator of osteoclastogenesis. TER has been shown to possess extensive biological and pharmacological benefits; however, its effects on bone metabolism remain unclear. In this study, we investigated the effects of TER on the femoral bone metabolism using a mouse-ovariectomized osteoporosis model (OVX mice) and then on RANKL signal transduction using mouse bone marrow macrophages (mBMMs). In vivo administration of TER significantly improved bone density, bone mass, and trabecular number in OVX mice (p &lt; 0.01). In addition, TER suppressed TRAP and cathepsin-K expression in the tissue sections of OVX mice (p &lt; 0.01). In an in vitro study, TER suppressed RANKL-induced phosphorylation of PKCα/βII, which is involved in the expression of NFATc1 (p &lt; 0.05). The PKC inhibitor, GF109203X, also inhibited RANKL-induced osteoclastogenesis in mBMMs as well as TER. In addition, TER suppressed the expression of osteoclastogenesis-related genes, such as Ocstamp, Dcstamp, Calcr, Atp6v0d2, Oscar, and Itgb3 (p &lt; 0.01). These results provide promising evidence for the potential therapeutic application of TER as a novel treatment compound against osteoporosis.

DOI： 10.3389/fphar.2021.674366

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Cu-Catalyzed Dehydrogenative C–O Cyclization for the Synthesis of Furan-Fused Thienoacenes Reviewed

Koichi Mitsudo, Yoshiaki Kobashi, Kaito Nakata, Yuji Kurimoto, Eisuke Sato, Hiroki Mandai, Seiji Suga

Organic Letters 23 ( 11 ) 4322 - 4326 2021.5

Electrosynthesis of Phosphacycles via Dehydrogenative C–P Bond Formation Using DABCO as a Mediator Reviewed

Yuji Kurimoto, Jun Yamashita, Koichi Mitsudo, Eisuke Sato, Seiji Suga

Organic Letters 23 ( 8 ) 3120 - 3124 2021.4

Acylative Desymmetrization of Cyclic meso-1,3-Diols by Chiral DMAP Derivatives Reviewed

Hiroki Mandai, Tsubasa Hironaka, Koichi Mitsudo, Seiji Suga

Chemistry Letters 50 ( 3 ) 471 - 474 2021.3

Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles Reviewed

Hiroki Mandai, Ryuhei Shiomoto, Kazuki Fujii, Koichi Mitsudo, Seiji Suga

Organic Letters 23 ( 4 ) 1169 - 1174 2021.2

Acylative desymmetrization of glycerol derivatives by chiral dmap derivatives Reviewed

Hiroki Mandai, Kosuke Ashihara, Koichi Mitsudo, Seiji Suga

Heterocycles 102 ( 6 ) 1083 - 1090 2021

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

An efficient enantioselective acylative desymmetrization of glycerol was developed by using a chiral DMAP derivatives 1e having a 1,1-binaphthyl unit. The reactions required only 0.1 mol% of the catalyst and showed moderate to good enantioselectivity (up to 94:6 er). Control experiments revealed that the first acylation of a glycerol derivative proceeded selectively rather than the second acylation to give diacylate.

DOI： 10.3987/COM-21-14433

Scopus

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Synthesis, optical and electrochemical properties of 4,4′-bibenzo[c]thiophene derivatives Reviewed

Kotaro Obayashi, Keiichi Imato, Satoshi Aoyama, Toshiaki Enoki, Seiji Akiyama, Mio Ishida, Seiji Suga, Koichi Mitsudo, Yousuke Ooyama

RSC Advances 11 ( 31 ) 18870 - 18880 2021

Language：English Publishing type：Research paper (scientific journal) Publisher：Royal Society of Chemistry (RSC)

<p>4,4′-Bibenzo[<italic>c</italic>]thiophene <bold>4,4′-BBT</bold> and its silyl-substituted derivatives <bold>1,1′-Si-4,4′-BBT</bold> and <bold>1,1′,3,3′-Si-4,4′-BBT</bold> have been designed and developed as new π-building blocks.</p>

DOI： 10.1039/d1ra01189h

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Synthesis of 9-Substituted Fluorenols and Heteroring-fused Analogues by Intramolecular C–H Functionalization Reviewed

Yuji Kurimoto, Koichi Mitsudo, Seiji Suga

Chemistry Letters 50 ( 2 ) 378 - 381 2020.12

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

Abstract

A method for the selective synthesis of 9-substituted fluorenols (FOLs) was developed by suppressing intermolecular cyclization and promoting intramolecular C–H functionalization. This protocol was applied to the synthesis of heteroring-fused FOLs. Further, the obtained FOLs were converted to fulvenes by dehydration.

DOI： 10.1246/cl.200807

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Integrated Synthesis of Thienyl Thioethers and Thieno[3,2-b]thiophenes via 1-Benzothiophen-3(2H)-ones Invited Reviewed

Koichi Mitsudo, Nanae Habara, Yoshiaki Kobashi, Yuji Kurimoto, Hiroki Mandai, Seiji Suga

Synlett 31 ( 19 ) 1947 - 1952 2020.12

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：GEORG THIEME VERLAG KG

A one-pot procedure for the synthesis of thienyl thioethers is described. Several thienyl thioethers were synthesized by a TfOH-promoted Friedel-Crafts-type cyclization, a subsequent nucleophilic attack by an arenethiol, and dehydration. This protocol was successfully applied to the synthesis of thienoacene derivatives by using a Pd-catalyzed dehydrogenative cyclization.

DOI： 10.1055/s-0040-1707280

Web of Science

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The fungal metabolite (+)-terrein abrogates osteoclast differentiation via suppression of the RANKL signaling pathway through NFATc1 Reviewed

Saki Nakagawa, Kazuhiro Omori, Masaaki Nakayama, Hiroki Mandai, Satoshi Yamamoto, Hiroya Kobayashi, Hidefumi Sako, Kyosuke Sakaida, Hiroshi Yoshimura, Satoki Ishii, Soichiro Ibaragi, Kimito Hirai, Keisuke Yamashiro, Tadashi Yamamoto, Seiji Suga, Shogo Takashiba

International Immunopharmacology 83 106429 2020.6

Electrochemical Synthesis of Thienoacene Derivatives: Transition‐Metal‐Free Dehydrogenative C−S Coupling Promoted by a Halogen Mediator Reviewed

Koichi Mitsudo, Ren Matsuo, Toki Yonezawa, Haruka Inoue, Hiroki Mandai, Seiji Suga

Angewandte Chemie 132 ( 20 ) 7877 - 7881 2020.5

Electrochemical Synthesis of Thienoacene Derivatives: Transition-Metal-Free Dehydrogenative C-S Coupling Promoted by a Halogen Mediator Reviewed

Koichi Mitsudo, Ren Matsuo, Toki Yonezawa, Haruka Inoue, Hiroki Mandai, Seiji Suga

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 59 ( 20 ) 7803 - 7807 2020.5

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：WILEY-V C H VERLAG GMBH

The first electrochemical dehydrogenative C-S bond formation leading to thienoacene derivatives is described. Several thienoacene derivatives were synthesized by dehydrogenative C-H/S-H coupling. The addition of (Bu4NBr)-Bu-n, which catalytically promoted the reaction as a halogen mediator, was essential.

DOI： 10.1002/anie.202001149

Web of Science

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Preface

Seiji Suga

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 78 ( 4 ) 291 - 291 2020.4

1,10-Phenanthroline- or Electron-Promoted Cyanation of Aryl Iodides Invited Reviewed

Koichi Mitsudo, Kazuki Yoshioka, Takayuki Hirata, Hiroki Mandai, Koji Midorikawa, Seiji Suga

Synlett 30 ( 10 ) 1209 - 1214 2019.6

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：GEORG THIEME VERLAG KG

A 1,10-phenanthroline-promoted cyanation of aryl iodides has been developed. 1,10-Phenanthroline worked as an organocatalyst for the reaction of aryl iodides with tetraalkylammonium cyanide to afford aryl cyanides. A similar reaction occurred through an electroreductive process.

DOI： 10.1055/s-0037-1611793

Web of Science

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Iodide-Mediated or Iodide-Catalyzed Demethylation and Friedel-Crafts C-H Borylative Cyclization Leading to Thiophene-Fused 1,2-Oxaborine Derivatives Reviewed

Keisuke Shigemori, Momoka Watanabe, Julie Kong, Koichi Mitsudo, Atsushi Wakamiya, Hiroki Mandai, Seiji Suga

Organic Letters 21 ( 7 ) 2171 - 2175 2019.4

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

The first synthesis of dithieno-1,2-oxaborine derivatives was achieved via iodide-mediated or iodide-catalyzed demethylation of 3-methoxy-2,2'-bithiophene and subsequent C-H borylation. A wide variety of thiophene-fused oxaborines could be synthesized by the procedure.

DOI： 10.1021/acs.orglett.9b00485

Web of Science

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Enantioselective Acyl Migration Reactions of Furanyl Carbonates with Chiral DMAP Derivatives Reviewed

Kazuki Fujii, Koichi Mitsudo, Hiroki Mandai, Toshinobu Korenaga, Seiji Suga

CHEMISTRY-A EUROPEAN JOURNAL 25 ( 9 ) 2208 - 2212 2019.2

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：WILEY-V C H VERLAG GMBH

An efficient enantioselective acyl migration reaction of furanyl carbonates was developed to construct all-carbon quaternary stereogenic centers. In some cases, the reactions required only 0.05 mol% (minimum 500 ppm) of catalyst and showed a high turnover frequency value (TOF; 3640 h(-1)). Multigram-scale reactions (10 grams) also proceeded with high enantioselectivity (> 99:1 e.r.) in quantitative yield. The catalyst was robust and easily recovered in 98% yield. A wide range of functional groups were tolerated (15 examples, > 98% yield, up to > 99:1 e.r.), and a variety of optically active 3,3'-disubstituted benzofuranone derivatives, which are useful intermediates for the synthesis of natural products and pharmaceuticals, were efficiently obtained. Control experiments on the catalyst structure (e.g., catalyst 1 a vs. 1 a' and 1 a") and computational calculations revealed that both the catalytic activity and enantioselectivity should be enhanced by hydrogen bonding between catalyst and substrate. Moreover, this system was applied to the challenging gamma-selective acyl migration reaction of furanyl carbonates with high gamma-selectivity and high enantioselectivity (a:gamma=10:90, 95:5 e.r.).

DOI： 10.1002/chem.201806050

Web of Science

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Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative Reviewed

Hiroki Mandai, Kosuke Ashihara, Koichi Mitsudo, Seiji Suga

Chemistry Letters 47 ( 11 ) 1360 - 1363 2018.11

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

We developed an enantioselective desymmetrization of 1,3-diols by a chiral N,N-dimethyl-4-aminopyridine (DMAP) derivative containing a 1,1'-binaphthyl with tert-alcohol units. The reactions required only 0.1 mol % of catalyst and showed moderate to high chemoselectivity (monoacylation vs. diacylation) and enantioselectivity (14 examples, up to 95:5 er). Several control experiments revealed that diol units in both the substrate and the catalyst are important to achieve high enantioselectivity.

DOI： 10.1246/cl.180697

Web of Science

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Fungal metabolite (+)-terrein suppresses IL-6/sIL-6R-induced CSF1 secretion by inhibiting JAK1 phosphorylation in human gingival fibroblasts Reviewed

Satoshi Yamamoto, Kazuhiro Omori, Hiroki Mandai, Masaaki Nakayama, Saki Nakagawa, Hiroya Kobayashi, Tadashi Kunimine, Hiroshi Yoshimura, Kyosuke Sakaida, Hidefumi Sako, Soichiro Ibaragi, Tadashi Yamamoto, Hiroshi Maeda, Seiji Suga, Shogo Takashiba

Heliyon 4 ( 11 ) e00979 2018.11

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Papers - SUGA Seiji