Updated on 2025/09/30

写真a

 
MIZOGUCHI Haruki
 
Organization
Faculty of Environmental, Life, Natural Science and Technology Associate Professor
Position
Associate Professor
External link

Degree

  • 博士(理学) ( 北海道大学 )

Research Interests

  • 天然物化学

  • Organoboron chemistry

Research Areas

  • Nanotechnology/Materials / Synthetic organic chemistry

  • Life Science / Bioorganic chemistry  / 有機化学

  • Nanotechnology/Materials / Chemistry and chemical methodology of biomolecules

  • Life Science / Pharmaceutical chemistry and drug development sciences

Education

  • Hokkaido University   大学院総合化学院   総合化学専攻

    2010.4 - 2013.3

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  • Hokkaido University   大学院理学院   化学専攻

    2008.4 - 2010.3

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  • Hokkaido University   理学部   化学科

    2004.4 - 2008.3

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  • Nagoya University    

    2001.4 - 2004.3

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Research History

  • Okayama University   学術研究院環境生命自然科学学域   Associate Professor

    2023.3

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    Notes:改組のため所属名称変更

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  • Okayama University   Graduate School of Natural Science and Technology   Associate Professor

    2021.4

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    Country:Japan

  • Okayama University   The Graduate School of Natural Science and Technology   Associate Professor

    2021.4 - 2022.3

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  • Okayama University   Graduate School of Natural Science and Technology   Assistant Professor

    2017.12 - 2021.3

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  • Dartmouth College   Department of Chemistry   Postdoctoral fellow

    2013.12 - 2017.11

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  • Hokkaido University   Faculty of Science   Postdoctoral researcher

    2013.4 - 2013.10

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Professional Memberships

Committee Memberships

  • 天然物化学談話会   世話人  

    2018   

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Papers

  • Development of a Vinylated Cyclic Allene: A Fleeting Strained Diene for the Diels–Alder Reaction

    Haruki Mizoguchi, Takumi Obata, Taiki Hirai, Manaka Komatsu, Akira Sakakura

    Angewandte Chemie International Edition   64 ( 33 )   2025.6

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

    Abstract

    Fleeting molecules possessing strained multiple bonds are important components in organic synthesis due to their ability to undergo various chemical reactions driven by the release of strain energy. Although the use of strained π‐bonds as 2π components, represented by dienophiles in Diels–Alder reactions, has been well studied, “the strained diene (4π component) approach” for molecular construction remains underexplored. Herein, we report the design of a vinyl cyclic allene (1‐vinyl‐1,2‐cyclohexadiene) as a highly reactive strained diene and the development of its Diels–Alder reactions. Experimental and computational studies of vinyl cyclic allenes revealed that this diene system undergoes cycloaddition with dienophiles regio‐ and stereoselectively under mild reaction conditions. These studies also provide insight into the reactivity and selectivity of the system. The strained diene approach enables the convergent construction of polycyclic molecules through bond disconnections distinct from conventional retrosynthetic analysis, thus offering an efficient strategy for the assembly of functional molecules.

    DOI: 10.1002/anie.202510319

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  • Synthesis of an angular triquinane structure based on a stereoselective decarboxylative Giese reaction at an angular position in a diquinane skeleton

    Naochika Matsumaru, Takumu Nishitani, Haruki Mizoguchi, Akira Sakakura

    Tetrahedron   178   134612 - 134612   2025.6

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

    DOI: 10.1016/j.tet.2025.134612

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  • Rapid construction of a diterpene-inspired tetracyclic skeleton bearing bicyclo[3.2.1]octane rings based on desymmetrization of 1,3-diketones

    Hidetoshi Kamada, Haruki Mizoguchi, Akira Sakakura

    Tetrahedron Letters   157   155470 - 155470   2025.2

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

    DOI: 10.1016/j.tetlet.2025.155470

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  • Visible-Light-Photoexcited Palladium-Catalyzed Silylmethylation of Benzyl Alcohol Derivatives Invited Reviewed

    Haruki Mizoguchi, Ryuji Yoshida, Haruka Ikeda, Akira Sakakura

    Synlett   34 ( 20 )   2451 - 2454   2023.7

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

    Abstract

    An intramolecular C–H silylmethylation of benzylic alcohol derivatives catalyzed by a visible-light-photoexcited palladium complex was developed. Irradiation of the palladium complex with blue LEDs resulted in efficient activation of a C–I bond, and subsequent intramolecular radical arylation afforded siloxacycle products. Selective protonation or oxidation of the C–Si bond of the cyclized materials afforded ortho-methylated and ortho-hydroxymethylated derivatives of the benzylic alcohol derivatives.

    DOI: 10.1055/s-0042-1752736

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  • Enantioselective construction of β-hydroxy-α,α-disubstituted α-amino acid derivatives via direct aldol reaction of α-imino esters Reviewed

    Yuya Araki, Masato Hanada, Yoshiko Iguchi, Haruki Mizoguchi, Akira Sakakura

    Tetrahedron   110   132695 - 132695   2022.3

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    DOI: 10.1016/j.tet.2022.132695

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  • Annulative coupling of vinylboronic esters: aryne-triggered 1,2-metallate rearrangement Reviewed

    Haruki Mizoguchi, Hidetoshi Kamada, Kazuki Morimoto, Ryuji Yoshida, Akira Sakakura

    Chemical Science   13 ( 33 )   9580 - 9585   2022

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

    DOI: 10.1039/d2sc02623f

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  • Strain-Release Difunctionalization of C–C σ- and π-bonds of an Organoboron Ate-Complex through 1,2-Metallate Rearrangement Reviewed

    Haruki Mizoguchi, Akira Sakakura

    Chemistry Letters   50   792 - 799   2021.1

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

  • Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate Reviewed

    Haruki Mizoguchi, Masaya Seriua, Akira Sakakura

    Chemical Communications   56   15545 - 15548   2020.11

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

  • Kinetic Resolution of α-Nitrolactones by Catalytic Asymmetric Hydrolysis or Ester–Amide Exchange Reaction Reviewed

    Akira Sakakura, Ryota Nakao, Yudai Fujii, Ichiro Hayakawa, Haruki Mizoguchi

    Synlett   31 ( 20 )   2018 - 2022   2020.10

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    Publishing type:Research paper (scientific journal)   Publisher:Georg Thieme Verlag KG  

    <title>Abstract</title>
    C
    1-Symmetric chiral ammonium salt catalysts induced a kinetic resolution of racemic α-nitrolactones through an asymmetric ester–amide exchange reaction. The corresponding amides were obtained with high enantioselectivities and high S (= k
    fast/k
    slow) values. This reaction system is a useful approach for obtaining carbocyclic quaternary α-nitroamides as chiral building blocks.

    DOI: 10.1055/s-0040-1707303

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  • Enantioselective Diels–Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts Reviewed

    Akira Sakakura, Yudai Fujii, Ryota Nakao, Saki Sugihara, Keita Fujita, Yuya Araki, Takayuki Kudoh, Ichiro Hayakawa, Haruki Mizoguchi

    Synlett   31 ( 20 )   2013 - 2017   2020.10

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    Publishing type:Research paper (scientific journal)   Publisher:Georg Thieme Verlag KG  

    <title>Abstract</title>An enantioselective Diels–Alder reaction of 3-nitrocoumarins has been developed. A tryptophan-derived C
    1-symmetric organoammonium thiourea catalyst promoted the reaction of 3-nitrocoumarins with Danishefsky’s diene to give the corresponding adducts with good enantioselectivity (up to 94% ee). One of the resulting adducts was converted into a chiral carbocyclic quaternary β-amino alcohol.

    DOI: 10.1055/s-0040-1707302

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  • Enantioselective Diels–Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts Reviewed

    Yudai Fujii, Ryota Nakao, Saki Sugihara, Keita Fujita, Yuya Araki, Takayuki Kudoh, Ichiro Hayakawa, Haruki Mizoguchi, Akira Sakakura

    Synlett   31   2013 - 2017   2020.10

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

  • Kinetic Resolution of α-Nitrolactones by Catalytic Asymmetric Hydrolysis or Ester–Amide Exchange Reaction Reviewed

    Ryota Nakao, Yudai Fujii, Ichiro Hayakawa, Haruki Mizoguchi, Akira Sakakura

    Synlett   31   2018 - 2020   2020.10

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

  • Rapid and Systematic Exploration of Chemical Space Relevant to Artemisinins: Anti-malarial Activities of Skeletally Diversified Tetracyclic Peroxides and 6-Aza-artemisinins. Reviewed International journal

    Karunakar Reddy Bonepally, Norihito Takahashi, Naoya Matsuoka, Hikari Koi, Haruki Mizoguchi, Takahisa Hiruma, Kyohei Ochiai, Shun Suzuki, Yutaka Yamagishi, Hideaki Oikawa, Aki Ishiyama, Rei Hokari, Masato Iwatsuki, Kazuhiko Otoguro, Satoshi O Mura, Nobutaka Kato, Hiroki Oguri

    The Journal of organic chemistry   85 ( 15 )   9694 - 9712   2020.8

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    To achieve both structural changes and rapid synthesis of the tetracyclic scaffold relevant to artemisinins, we explored two kinds of de novo synthetic approaches that generate both skeletally diversified tetracyclic peroxides and 6-aza-artemisinins. The anti-malarial activities of the tetracyclic peroxides with distinct skeletal arrays, however, were moderate and far inferior to artemisinins. Given the privileged scaffold of artemisinins, we next envisioned element implantation at the C6 position with a nitrogen without the trimmings of substituents and functional groups. This molecular design allowed the deep-seated structural modification of the hitherto unexplored cyclohexane moiety (C-ring) while keeping the three-dimensional structure of artemisinins. Notably, this approach induced dramatic changes of retrosynthetic transforms that allow an expeditious catalytic asymmetric synthesis with generation of substitutional variations at three sites (N6, C9, and C3) of the 6-aza-artemisinins. These de novo synthetic approaches led to the lead discovery with substantial intensification of the in vivo activities, which undermine the prevailing notion that the C-ring of artemisinins appears to be merely a structural unit but to be a functional area as the anti-malarial pharmacophore. Furthermore, we unexpectedly found that racemic 6-aza-artemisinin (33) exerted exceedingly potent in vivo efficacies superior to the chiral one and the first-line drug, artesunate.

    DOI: 10.1021/acs.joc.0c01017

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  • Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate Reviewed

    Haruki Mizoguchi, Masaya Seriu, Akira Sakakura

    Chemical Communications   56 ( 99 )   15545 - 15548   2020

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

    DOI: 10.1039/d0cc07134j

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  • Formal Total Synthesis of Manzacidin B via Sequential Diastereodivergent Henry Reaction Reviewed

    Yuya Araki, Natsumi Miyoshi, Kazuki Morimoto, Takayuki Kudoh, Haruki Mizoguchi, Akira Sakakura

    The Journal of Organic Chemistry   ASAP   2019.12

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  • Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with alpha-(Acyloxy)acroleins Catalyzed by Dipeptide-Derived Chiral Tri- or Diammonium Salts Reviewed

    Chihiro Kidou, Haruki Mizoguchi, Tatsuo Nehira, Akira Sakakura

    SYNLETT   30 ( 15 )   1835 - 1839   2019.9

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

    DOI: 10.1055/s-0039-1690133

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  • Thioureas as Highly Active Catalysts for Biomimetic Bromocyclization of Geranyl Derivatives Reviewed

    Miyuki Terazaki, Kei-ichi Shiomoto, Haruki Mizoguchi, Akira Sakakura

    ORGANIC LETTERS   21 ( 7 )   2073 - 2076   2019.4

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    DOI: 10.1021/acs.orglett.9b00352

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  • Zn(OTf)2-mediated annulations of N-propargylated tetrahydrocarbolines: divergent synthesis of four distinct alkaloidal scaffolds Reviewed

    Sadaiwa Yorimoto, Akira Tsubouchi, Haruki Mizoguchi, Hideaki Oikawa, Yoshiaki Tsunekawa, Tomoya Ichino, Satoshi Maeda, Hiroki Oguri

    Chemical Science   10   5686 - 5698   2019

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  • Design and De Novo Synthesis of 6‐Aza-artemisinins Reviewed

    Karunakar Reddy Bonepally, Takahisa Hiruma, Haruki Mizoguchi, Kyohei Ochiai, Shun Suzuki, Hideaki Oikawa, Aki Ishiyama, Rei Hokari, Masato Iwatsuki, Kazuhiko Otoguro, Satoshi O̅mura, Hiroki Oguri

    Organic Letters   20   4667 - 4671   2018

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  • Stereo-controlled synthesis of functionalized tetrahydropyridines based on the cyanomethylation of 1,6-dihydropyridines and generation of anti-hepatitis C virus agents Reviewed

    Ryo Watanabe, Haruki Mizoguchi, Hideaki Oikawa, Hirofumi Ohashi, Koichi Watashi, Hiroki Oguri

    BIOORGANIC & MEDICINAL CHEMISTRY   25 ( 11 )   2851 - 2855   2017.6

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    DOI: 10.1016/j.bmc.2017.03.011

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  • Synthesis of Angularly Substituted trans-Fused Decalins through a Metallacycle-Mediated Annulative Cross-Coupling Cascade Reviewed

    Haruki Mizoguchi, Glenn C. Micalizio

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   55 ( 42 )   13099 - 13103   2016.10

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

    DOI: 10.1002/anie.201606962

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  • multipotent intermediate Reviewed

    Haruki Mizoguchi, Hiroki Oguri

    Journal of Synthetic Organic Chemistry JAPAN   74 ( 9 )   915   2016.9

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  • Acceleration of metallacycle-mediated alkyne-alkyne cross-coupling with TMSCl Reviewed

    James S. Cassidy, Haruki Mizoguchi, Glenn C. Micalizio

    TETRAHEDRON LETTERS   57 ( 34 )   3848 - 3850   2016.8

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    DOI: 10.1016/j.tetlet.2016.07.045

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  • LiOOt-Bu as a terminal oxidant in a titanium alkoxide-mediated [2+2+2] reaction cascade Reviewed

    Wan Shin Kim, Claudio Aquino, Haruki Mizoguchi, Glenn C. Micalizio

    TETRAHEDRON LETTERS   56 ( 23 )   3557 - 3559   2015.6

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    DOI: 10.1016/j.tetlet.2015.01.029

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  • Synthesis of Highly Functionalized Decalins via Metallacycle-Mediated Cross-Coupling Reviewed

    Haruki Mizoguchi, Glenn C. Micalizio

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   137 ( 20 )   6624 - 6628   2015.5

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    DOI: 10.1021/jacs.5b02107

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  • Synthesis of multiply substituted 1,6-dihydropyridines through Cu(I)-catalyzed 6-endo cyclization Reviewed

    Haruki Mizoguchi, Ryo Watanabe, Shintaro Minami, Hideaki Oikawa, Hiroki Oguri

    ORGANIC & BIOMOLECULAR CHEMISTRY   13 ( 21 )   5955 - 5963   2015

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    DOI: 10.1039/c5ob00356c

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  • Synthesis of Angularly Substituted Trans-Fused Hydroindanes by Convergent Coupling of Acyclic Precursors Reviewed

    Valer Jeso, Claudio Aquino, Xiayun Cheng, Haruki Mizoguchi, Mika Nakashige, Glenn C. Micalizio

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   136 ( 23 )   8209 - 8212   2014.6

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    DOI: 10.1021/ja504374j

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  • Biogenetically inspired synthesis and skeletal diversification of indole alkaloids Reviewed

    Haruki Mizoguchi, Hideaki Oikawa, Hiroki Oguri

    NATURE CHEMISTRY   6 ( 1 )   57 - 64   2014.1

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    DOI: 10.1038/NCHEM.1798

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  • Parallel and four-step synthesis of natural-product-inspired scaffolds through modular assembly and divergent cyclization Reviewed

    Hiroki Oguri, Haruki Mizoguchi, Hideaki Oikawa, Aki Ishiyama, Masato Iwatsuki, Kazuhiko Otoguro, Satoshi Omura

    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY   8   930 - 940   2012.6

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    DOI: 10.3762/bjoc.8.105

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  • Hg(OTf)(2)-catalyzed direct vinylation of tryptamines and versatile applications for tandem reactions Reviewed

    Haruki Mizoguchi, Hideaki Oikawa, Hiroki Oguri

    ORGANIC & BIOMOLECULAR CHEMISTRY   10 ( 21 )   4236 - 4242   2012

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    DOI: 10.1039/c2ob25236h

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  • 33 Divergent Synthesis of Multicyclic Alkaloids Inspired by Biosynthetic Strategy(Oral Presentation)

    Mizoguchi Haruki, Oguri Hiroki, Oikawa Hideaki

    Symposium on the Chemistry of Natural Products, symposium papers   ( 53 )   193 - 198   2011.9

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    Language:Japanese   Publisher:Symposium on the chemistry of natural products  

    Indole alkaloids composed of elaborated cyclic arrays have been one of the most valuable resources for discovering biologically active substances. To gain concise and flexible access to alkaloid analogs possessing natural and unexploited skeletons, we are developing a synthetic process based on divergent cyclizations inspired by the biogenic strategy generating structural diversity of natural products. With intentions to emulate the biosynthetic proposal of iboga and aspidosperma alkaloids, we designed a common dihydropyridine precursor 3 for divergent Diels-Alder reactions in either of two ways: (1) the dihydropyridine reacts as a diene leading to the iboga-type skeleton; (2) the dihydropyridine serves as a dienophile to form the aspidosperma-type skeleton. First of all, we developed an original protocol for constructing sensitive 1,6-dihydropyridine (DHP) rings employing a cationic Cu(I) catalyst. Next, the key precursor 21 for the Cu(I)-catalyzed DHP synthesis was successfully prepared through conjugate addition of the common intermediate 25 with methyl propiolate 20 and concomitant Hofmann elimination. The Cu(I)-catalyzed 1,6-DHP cyclization and subsequent Diels-Alder cycloaddition under mild conditions (45℃) allowed a cascade synthesis of iboga-type skeleton 28. Meanwhile, divergent cyclization proceeded to furnish ngouniensine-type skeleton 29 by the simple modification of reaction temperature (100℃). Furthermore, the reaction site of 25 with 20 was altered depending on the solvents to produce a distinct precursor for the Cu(I)-catalyzed cyclization, which allowed successful construction of a novel tetracyclic skeleton 31. We also achieved total synthesis of (±)-catharanthine 34 through protecting group-free 9-step sequence in order to demonstrate applicability and potential of the currently developed synthetic process efficiently generating complexity and diversity of natural product relevant scaffolds in a programmable fashion.

    DOI: 10.24496/tennenyuki.53.0_193

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  • Divergent and Expeditious Access to Fused Skeletons Inspired by Indole Alkaloids and Transtaganolides Reviewed

    Haruki Mizoguchi, Hiroki Oguri, Kiyoshi Tsuge, Hideaki Oikawa

    ORGANIC LETTERS   11 ( 14 )   3016 - 3019   2009.7

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    DOI: 10.1021/ol901020a

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MISC

  • ビシクロ[3.2.1]オクタン縮環型天然物グラヤナンジテルペノイドの全合成 Invited

    溝口玄樹

    化学と工業   76 ( 4 )   2023.4

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  • Strain-release Difunctionalization of C–C σ- and π-bonds of an Organoboron Ate-complex through 1,2-Metallate Rearrangement Invited Reviewed

    Haruki Mizoguchi, Akira Sakakura

    Chemistry Letters   50 ( 4 )   792 - 799   2021.4

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Article, review, commentary, editorial, etc. (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.200926

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  • 生理活性発現のための活性化型構造の提案:Myrocin Gの合成 Reviewed

    溝口 玄樹

    ファルマシア   55   68 - 69   2019

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  • チタンを用いるクロスカップリング ーステロイドやテルペノイド合成への新たなアプローチー

    溝口 玄樹, 坂倉 彰

    化学(化学同人)   73   68 - 69   2018.8

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  • The Development of Alkoxide-Directed Metallacycle-Mediated Annulative Cross-Coupling Chemistry Invited Reviewed

    Glenn C. Micalizio, Haruki Mizoguchi

    ISRAEL JOURNAL OF CHEMISTRY   57 ( 3-4 )   228 - 238   2017.4

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    Language:English   Publishing type:Book review, literature introduction, etc.  

    DOI: 10.1002/ijch.201600098

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  • Recent Developments in Synthetic Strategies toward Highly Oxygenated Steroids Cardenolides Reviewed

    Haruki Mizoguchi

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   75 ( 3 )   253 - 254   2017.3

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    Language:Japanese   Publishing type:Book review, literature introduction, etc.  

    DOI: 10.5059/yukigoseikyokaishi.75.253

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  • Development of an Artificial Assembly Line Generating Skeletally Diverse Indole Alkaloids Inspired by Biogenetic Strategy Reviewed

    Haruki Mizoguchi, Hiroki Oguri

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   74 ( 9 )   854 - 865   2016.9

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    Language:Japanese   Publishing type:Book review, literature introduction, etc.  

    DOI: 10.5059/yukigoseikyokaishi.74.854

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  • インドールアルカロイドの骨格多様化合成―生合成に学ぶ分岐型合成戦略―

    溝口 玄樹, 大栗 博毅

    化学と生物   53   345 - 346   2014.6

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    Language:Japanese   Publishing type:Article, review, commentary, editorial, etc. (trade magazine, newspaper, online media)  

    DOI: 10.1271/kagakutoseibutsu.53.345

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  • 生合成経路を模倣した骨格多様化合成 –ニチニチソウに学ぶアルカロイド骨格の作り分け

    溝口 玄樹, 大栗 博毅

    化学(化学同人)   69 ( 5 )   12 - 17   2014.5

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    Language:Japanese   Publishing type:Article, review, commentary, editorial, etc. (trade magazine, newspaper, online media)   Publisher:化学同人  

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Presentations

  • ホウ素アート錯体のメタレート転位を利用する分子構築法の開発 Invited

    溝口玄樹

    2022年日本化学会中国四国支部大会 広島大会  2022.11.13 

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    Event date: 2022.11.12 - 2022.11.13

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  • ビニル環状アレンを高活性ジエン種として用いる Diels-Alder 反応の開発

    溝口玄樹, 小幡匠, 平井大貴, 小松万菜佳, 坂倉彰

    第51回 有機典型元素化学討論会  2024.12.7 

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  • ホウ素が主役となるアートな反応の開発を目指して Invited

    溝口玄樹

    第8回有機若手ワークショップ  2023.12.20 

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    Language:Japanese   Presentation type:Symposium, workshop panel (nominated)  

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  • ホウ素アート錯体の1,2-メタレート転位を活用するカップリング反応の開発 Invited

    溝口玄樹

    若手研究者のための有機化学札幌セミナー  2021.11.17 

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  • α-ケトエステルの直截的不斉Mannich反応に有効なキラル銅(II)触媒の設計

    近藤真由,岩木伸穏,三宅麻由,溝口玄樹,坂倉彰

    日本化学会第101春季年会  2021.3.20 

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    Language:Japanese   Presentation type:Oral presentation (general)  

  • ビニルボロン酸エステルアート錯体とアラインを組み合わせる多置換アルキルボロン酸合成法の開発

    鎌田英寿,森本一樹,吉田竜二,溝口玄樹,坂倉彰

    日本化学会第101春季年会  2021.3.19 

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    Venue:オンライン開催  

  • キラル有機アンモニウム塩触媒を用いた3-ニトロクマリンのエナンチオ選択的Diels–Alder反応

    藤田啓太,杉原早紀,荒木雄也,早川一郎,溝口玄樹,坂倉彰

    日本化学会第101春季年会  2021.3.19 

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    Venue:オンライン開催  

  • 光励起したパラジウム触媒によるベンジルアルコール誘導体の分子内C-Hシリルメチル化反応の開発

    吉田竜士,池田遥香,溝口玄樹,坂倉彰

    日本化学会第101春季年会  2021.3.19 

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    Venue:オンライン開催  

  • アラインをトリガーとするビニルボロン酸エステルアート錯体の1,2-メタレート転位における基質適用範囲および反応機構研究

    溝口玄樹,森本一樹,鎌田英寿,吉田竜士,坂倉彰

    日本化学会第101春季年会  2021.3.19 

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    Venue:オンライン開催  

  • アラインをトリガーとするビニルボロン酸エステルアート錯体の1,2-メタレート転位における基質適用範囲および反応機構研究

    溝口玄樹, 森本一樹, 鎌田英寿, 吉田竜士, 坂倉彰

    日本化学会第101春季年会  2021.3.19 

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  • ホウ素アート錯体の1,2-メタレート転位を活用する多置換シクロプロピルボロン酸の立体選択的構築

    芹生将哉,溝口玄樹,坂倉彰

    日本化学会第100春季年会  2020.3.22 

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    Venue:COVID-19のため学会中止,講演予稿集の発行により発表成立  

  • 非対称化を伴う還元的Heck反応による高酸化型テルペノイド骨格の構築

    吉田竜士,久保葵,溝口玄樹,坂倉彰

    日本化学会第100春季年会  2020.3.22 

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    Venue:COVID-19のため学会中止,講演予稿集の発行により発表成立  

  • キラルルイス酸触媒を用いたα,α-二置換-β-ヒドロキシ-α-アミノ酸構造の立体選択的構築法の開発

    花田将人,荒木雄也,溝口玄樹,坂倉彰

    日本化学会第100春季年会  2020.3.22 

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    Venue:COVID-19のため学会中止,講演予稿集の発行により発表成立  

  • Metallacycle Mediated Annulative Cross-Coupling for the Synthesis of Angularly Substituted Stereodefined Declines

    Haruki Mizoguchi, Glenn C. MIcalizio

    2019.3.17 

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  • Metallacycle-mediated synthesis of highly functionalized decalins International conference

    Haruki Mizoguchi, Glenn C. Micalizio

    National Organic Symposium 2017  2017 

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  • Metallacycle-mediated synthesis of highly functionalized decalins International conference

    Haruki Mizoguchi, Glenn C. Micalizio

    ACS 250th National Meeting, Boston, MA  2015 

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  • Biogenetically inspired synthesis and skeletal diversification of indole alkaloids International conference

    Haruki Mizoguchi, Hideaki Oikawa, Hiroki Oguri

    ACS 250th National Meeting, Boston, MA  2015 

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  • Biogenetically inspired synthesis and skeletal diversification of indole alkaloids International conference

    Haruki Mizoguchi, Hideaki Oikawa, Hiroki Oguri

    REAXYS INSPIRING CHEMISTRY CONFERENCE 2014, Grindelwald  2014 

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  • 生合成に類似した骨格多様化戦略によるインドールアルカロイド群の合成

    溝口 玄樹, 大栗 博毅, 及川 英秋

    日本化学会第 93 春季年会  2013.3 

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  • Development of a biogenetically inspired assembly line for skeletally diverse indole alkaloids International conference

    Haruki Mizoguchi, Hideaki Oikawa, Hiroki Oguri

    13th International Conference of the Chemistry of Antibiotics and other bioactive compounds, Yamanashi  2013 

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  • 骨格改変戦略によるインドールアルカロイド類の迅速合成

    溝口 玄樹, 大栗博毅, 及川英秋

    第 102 回 有機合成シンポジウム  2012.11 

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  • インドールアルカロイド群の骨格改変合成

    溝口 玄樹, 大栗 博毅, 及川 英秋

    第 42 回 複素環化学討論会  2012.10 

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  • 多環式アルカロイド群の分岐型迅速合成プロセス:生合成を模倣した多様性獲得戦略

    溝口 玄樹, 大栗 博毅, 及川 英秋

    日本化学会第 92 春季年会  2012.3 

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  • Divergent Synthesis of Multicyclic Alkaloids Inspired by Biosynthetic Strategy International conference

    Haruki Mizoguchi, Hiroki Oguri, Hideaki Oikawa

    11th iCeMS International Symposium  2011.12 

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  • 多環式アルカロイド群の分岐型迅速合成プロセス:生合成を模倣した構造多様化戦略

    溝口 玄樹, 大栗 博毅, 及川 英秋

    第 53 回 天然有機化合物討論会  2011.9 

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  • アスピドスペルマ/イボガ型アルカロイド骨格の分岐型短段階構築法の開発:生合成を模倣した構造多様化戦 略

    溝口 玄樹, 大栗 博毅, 及川 英秋

    日本化学会第 91 春季年会  2011.3 

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  • Divergent and biomimetic synthesis of the aspidosperma/iboga-type alkaloids and their analogs International conference

    Haruki Mizoguchi, Hiroki Oguri, Hideaki OikawaMIZOGUCHI Haruki

    2010 The International Chemical Congress of Pacific Basin Societies  2010.12 

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  • インドールアルカロイドの短段階合成と構造多様化

    溝口 玄樹, 大栗 博毅, 及川 英秋

    第 1 回大津会議 Otsu Conference 2010 ‐有機化学の夢を語る‐  2010.10 

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  • アスピドスペルマ/イボガ型アルカロイド骨格の短段階構築法の開発

    溝口 玄樹, 大栗 博毅, 及川 英秋

    第 22 回 万有札幌シンポジウム  2010.7 

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  • アスピドスペルマ/イボガ型アルカロイド骨格の短段階構築法の開発:生合成を模倣した分岐型合成戦略

    溝口 玄樹, 大栗 博毅, 及川 英秋

    日本化学会第 90 春季年会  2010.3 

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  • 多環性アルカロイド様低分子ライブラリーの構築:環化モード制御による構造多様化

    溝口 玄樹, 大栗 博毅, 及川 英秋

    日本ケミカルバイオロジー学会 第 4 回年会  2009.5 

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  • 多環性アルカロイド様低分子群の構築:環化モード制御による構造多様化

    溝口 玄樹, 大栗 博毅, 及川 英秋

    日本化学会第 89 春季年会  2009.3 

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  • アラインをトリガーとするビニルボロン酸エステルアート錯体の歪み開放型メタレート転位反応の開発

    溝口玄樹, 森本一樹, 豊田耕平, 仲宗根礼子, 坂倉彰

    日本化学会第100春季年会 

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Awards

  • 有機合成化学奨励賞

    2024.12   有機合成化学協会   ホウ素アート錯体の特性を活かした分子構築法の開発

    溝口玄樹

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  • 有機合成化学協会研究企画賞(中外製薬研究企画賞)

    2018.12  

    溝口 玄樹

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  • 18th Young Scientist's Research Award in Natural Product Chemistry

    2018.7  

    MIZOGUCHI Haruki

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  • 2014 Reaxys PhD Prize Finalist

    2014.9  

    MIZOGUCHI Haruki

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  • 102nd Symposium on The Society of Organic Chemistry, poster award

    2012.11  

    MIZOGUCHI Haruki

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  • Otsu Conference 2010 (Banyu Life Science Foundation International)

    2010.10  

    MIZOGUCHI Haruki

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  • 22th Banyu Sapporo Symposium poster award

    2010.7  

    MIZOGUCHI Haruki

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  • Hokkaido University Clark Award

    2008.3  

    MIZOGUCHI Haruki

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Research Projects

  • ホウ素ドープ型天然物フレームワーク概念に基づく環境応答型低分子リガンドの創出

    2024.04 - 2027.03

    公益財団法人 内藤記念科学振興財団  2023年度 内藤記念次世代育成支援研究助成金 

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  • 1,2-メタレート転位の立体制御を基盤とするホウ素アート錯体のカップリング反応の開発

    Grant number:23K04734  2023.04 - 2026.03

    日本学術振興会  科学研究費助成事業  基盤研究(C)

    溝口 玄樹

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    Grant amount:\4680000 ( Direct expense: \3600000 、 Indirect expense:\1080000 )

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  • 非対称化を鍵とするビシクロ[3.2.1]オクタン環含有テルペノイドの迅速合成

    2022.04 - 2023.03

    ウエスコ学術振興財団  研究活動費助成事業 

    溝口玄樹

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  • 有機分子触媒と光励起パラジウム錯体の 協働触媒系によるラジカル不斉合成

    2021.04 - 2022.03

    公益財団法人 岡山工学振興会  岡山工学振興会科学技術賞 一般研究 

    溝口玄樹

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  • アルコキシラジカル開裂を起点とする環化付加型反応によるビシクロ環含有天然物の合成

    2020.09 - 2021.08

    住友財団  2020年度基礎科学研究助成 

    溝口玄樹

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  • 天然物合成技術を基盤とする「天然物マテリアルサイエンス」推進拠点の構築

    2020.09 - 2021.03

    岡山大学  次世代研究拠点形成支援事業「令和2年度岡山大学次世代研究育成グループ」 

    溝口玄樹, 中山淳, 寄立麻琴, 佐藤英祐

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  • ホウ素アート錯体のメタレート転位を歪んだπ結合で駆動する多成分連結型反応の開発

    Grant number:20K15282  2020.04 - 2023.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Early-Career Scientists  Grant-in-Aid for Early-Career Scientists

    溝口玄樹

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    Grant amount:\4030000 ( Direct expense: \3100000 、 Indirect expense:\930000 )

    有機ホウ素分子は現代の有機化学において不可欠な化学種であり、構造多様な有機ホウ素を供給できる合成技術の重要性はますます高まっている。本研究では複雑で多彩な構造の有機ホウ素分子を簡便に構築可能な合成手法の開拓を目的として、ビニルホウ素アート錯体の1,2-メタレート転位を伴うカップリング反応に注目した。
    本研究では、歪んだπ結合を持つアラインに注目し、これをビニルボロン酸エステルアート錯体に対し作用させることでメタレート転位を伴うカップリング反応を開発している。ここでは、三重結合が開裂することで新たな反応活性種であるアリールアニオンが生じ、これが近傍のホウ素へと環化することでボリン酸エステルアート錯体を与えており、[3+2]型のアニュレーション反応となっていることが特徴である。本反応について、反応条件の最適化や基質適用範囲の調査を行ったことを昨年度の報告書で報告した。
    本年度の研究では、反応についての更なる知見を得るため、立体選択性に関する調査と反応機構解析を行った。その結果、本反応が段階的なシン選択的反応であることを見出した。これについてはDFT計算を用いた反応機構の解析も行なっており、これらの成果をまとめた論文を投稿中である。
    また、歪みを持つシクロプロペニルボロン酸エステルアート錯体を用いるメタレート転位反応の開発も行なっており、本手法を足掛かりにジビニルシクロプロパン構造を発生させ、Cope転位により7員環構造が構築できることも見出した。

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  • ホウ素アート錯体の歪み開放型メタレート転位を鍵とするカップリング反応の開発

    2020.04 - 2021.03

    宇部興産学術振興財団  学術奨励賞 

    溝口玄樹

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  • ホウ素アート錯体の. 1,2-メタレート転位を精密制御する多官能性分子骨格の構築

    2019.04 - 2021.03

    有機合成化学協会  研究企画賞(中外製薬研究企画賞) 

    溝口玄樹

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  • メタレート転位を活用する三次元有機ボロン酸の構築

    2019.03 - 2020.04

    公益財団法人 上原記念生命科学財団  研究奨励金 

    溝口 玄樹

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  • 環状ホウ素アート錯体の立体選択的 1,2-メタレート転位反応の開発

    2018.09 - 2019.08

    公益財団法人 戸部眞紀財団  平成 30 年度 研究助成金 

    溝口 玄樹

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  • 環状ホウ素アート錯体の 1,2-メタレート転位を鍵とする多官能性分子骨格の迅速合成

    2018 - 2019

    日本学術振興会  平成 30 年度科学研究費補助金(研究スタート支援) 

    溝口 玄樹

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  • アルコキシドを配向基として精密制御するアルケニルボロン酸アート錯体の 1,2-メタレ ート転位

    2018

    公益財団法人 岡山工学振興会  平成 30 年度 学術研究助成(奨励研究) 

    溝口 玄樹

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  • メタラサイクルを活用する立体選択的炭素環構築法の開発と生理活性テルペノイドの合成

    2015 - 2016

    日本学術振興会  海外特別研究員 

    溝口 玄樹

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  • 還元的カップリングを 鍵とする天然物合成

    2013.12 - 2014.11

    公益財団法人 上原記念生命科学財団  海外留学助成ポストドクトラルフェローシップ 

    溝口 玄樹

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  • インドールアルカロイドの短段階全合成と環化モード制御による構造多様化

    2010 - 2012

    日本学術振興会  特別研究員(DC1)奨励費 

    溝口 玄樹

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Class subject in charge

  • Experiment for Chemistry and Biotechnology 1 (2024academic year) 1st and 2nd semester  - 月5~8

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  • Chemistry of Natural Product Synthesis (2023academic year) Late  - その他

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  • Organic Chemistry Ⅴ (2023academic year) Third semester  - 月2,木6

  • Organic Chemistry 2 (2023academic year) Third semester  - 月1~2,木5~6

  • Organic Chemistry 3 (2023academic year) Third semester  - 月1~2,木5~6

  • Material Process Experiment 1 (2023academic year) Fourth semester  - 月5~8

  • Material Process Experiment 2 (2023academic year) 1st semester  - 月5~8,木5~8

  • Advanced Study (2023academic year) Other  - その他

  • Biofunctional Organic Chemistry (2023academic year) Late  - その他

  • Biotechnology experiment 1 (2023academic year) Fourth semester  - 月5~8

  • Bioorganic Chemistry (2023academic year) Late  - その他

  • Seminar in Bioorganic Chemistry (2023academic year) Year-round  - その他

  • Seminar in Bioorganic Chemistry (2023academic year) Year-round  - その他

  • Experiment for Chemistry and Biotechnology 2 (2022academic year) Fourth semester  - 月5~8

  • Synthetic Chemistry Experiment 1 (2022academic year) Fourth semester  - 月5~8

  • Synthetic Chemistry Experiment 2 (2022academic year) 1st semester  - 月5~8,木5~8

  • Synthetic Chemistry Experiment 2 (2022academic year) 1st semester  - 月5~8,木5~8

  • Chemistry of Natural Product Synthesis (2022academic year) Late  - その他

  • Internship in Applied Chemistry (2022academic year) Prophase  - その他

  • Seminar on Applied Chemistry 1 (2022academic year) Prophase  - その他

  • Seminar on Applied Chemistry 2 (2022academic year) Late  - その他

  • Research Works for Master Thesis on Applied Chemistry (2022academic year) Year-round  - その他

  • Organic Chemistry and its Exercises 2 (2022academic year) Third semester  - 月1~2,木5~6

  • Organic Chemistry 2 (2022academic year) Third semester  - 月1~2,木5~6

  • Organic Chemistry 3 (2022academic year) Third semester  - 月1~2,木5~6

  • Material Process Experiment 1 (2022academic year) Fourth semester  - 月5~8

  • Biotechnology experiment 1 (2022academic year) Fourth semester  - 月5~8

  • Seminar in Bioorganic Chemistry (2022academic year) Year-round  - その他

  • Bioactive Molecular Chemistry (2022academic year) Late  - 火1,火2

  • Synthetic Chemistry Experiment 1 (2021academic year) Fourth semester  - 月5,月6,月7,月8,木5,木6,木7,木8

  • Synthetic Chemistry Experiment 2 (2021academic year) 1st semester  - 月5,月6,月7,月8,木5,木6,木7,木8

  • Synthetic Chemistry Experiment 1 (2021academic year) Fourth semester  - 月5,月6,月7,月8,木5,木6,木7,木8

  • Synthetic Chemistry Experiment 2 (2021academic year) 1st semester  - 月5,月6,月7,月8,木5,木6,木7,木8

  • Chemistry of Natural Product Synthesis (2021academic year) Late  - その他

  • Internship in Applied Chemistry (2021academic year) Prophase  - その他

  • Seminar on Applied Chemistry 1 (2021academic year) Prophase  - その他

  • Seminar on Applied Chemistry 2 (2021academic year) Late  - その他

  • Research Works for Master Thesis on Applied Chemistry (2021academic year) Year-round  - その他

  • Organic Chemistry and its Exercises 2 (2021academic year) Second semester  - 月3,月4,木1,木2

  • Organic Chemistry and its Exercises 2 (2021academic year) Second semester  - 月3,月4,木1,木2

  • Organic Chemistry 2 (2021academic year) Second semester  - 月3,月4,木1,木2

  • Organic Chemistry 2 (2021academic year) Second semester  - 月3,月4,木1,木2

  • Seminar in Bioorganic Chemistry (2021academic year) Year-round  - その他

  • Bioactive Molecular Chemistry (2021academic year) Late  - 火1,火2

  • Frontier Synthetic Chemistry (2020academic year) Late  - 金1,金2

  • Synthetic Chemistry Experiment 1 (2020academic year) Fourth semester  - 月4,月5,月6,月7,木4,木5,木6,木7

  • Synthetic Chemistry Experiment 2 (2020academic year) 1st semester  - 月4,月5,月6,月7,木4,木5,木6,木7

  • Synthetic Chemistry Experiment 1 (2020academic year) Fourth semester  - 月4,月5,月6,月7,木4,木5,木6,木7

  • Synthetic Chemistry Experiment 2 (2020academic year) 1st semester  - 月4,月5,月6,月7,木4,木5,木6,木7

  • Internship in Applied Chemistry (2020academic year) Prophase  - その他

  • Seminar on Applied Chemistry 1 (2020academic year) Prophase  - その他

  • Seminar on Applied Chemistry 2 (2020academic year) Late  - その他

  • Research Works for Master Thesis on Applied Chemistry (2020academic year) Year-round  - その他

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