Updated on 2021/11/30

写真a

 
MIZOGUCHI Haruki
 
Organization
Faculty of 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 Universitry   Graduate School of Chemical Science and Technology  

    2010.4 - 2013.3

      More details

  • Hokkaido University   Graduate School of Science  

    2008.4 - 2010.3

      More details

  • Hokkaido Universitry    

    2004.4 - 2008.3

      More details

  • Nagoya University   School of Education  

    2001.4 - 2004.3

      More details

Research History

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

    2021.4

      More details

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

    2021.4

      More details

    Country:Japan

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

    2017.12 - 2021.3

      More details

  • Dartmouth College   Department of Chemistry   Postdoctoral fellow

    2013.12 - 2017.11

      More details

  • Hokkaido University   Faculty of Science   Postdoctoral researcher

    2013.4 - 2013.10

      More details

Professional Memberships

 

Papers

  • 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

     More details

    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

     More details

    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   2020.10

     More details

    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

    researchmap

  • 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   2020.10

     More details

    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

    researchmap

  • 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

     More details

    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

     More details

    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

     More details

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

    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

    PubMed

    researchmap

  • 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

     More details

    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    <p>A procedure converting tribromocyclopropane to densely functionalized β-selenocyclopropylboronic ester using the 1,2-metallate rearrangement of a boron ate-complex has been developed.</p>

    DOI: 10.1039/d0cc07134j

    researchmap

  • 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

     More details

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

    researchmap

  • 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

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:GEORG THIEME VERLAG KG  

    Organoammonium salts of dipeptide-derived chiral tri-amines or diamines with TfOH catalyzed the enantioselective 1,3-dipolar cycloaddition reactions of alpha-acyloxyacroleins with nitrones to give the corresponding adducts in good yields (up to 96%) and with high diastereo- and enantioselectivities (up to 89% ee). Although alpha-(p-methoxybenzoyloxy)acrolein is rather unstable under the reaction conditions, alpha-(3-pyrroline-1-carbonyloxy)acrolein is stable enough to be smoothly converted into the corresponding adducts with the aid of the chiral organoammonium salt catalysts.

    DOI: 10.1055/s-0039-1690133

    Web of Science

    researchmap

  • 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

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    Thioureas bearing electron-deficient aryl groups show high catalytic activity in the biomimetic bromocyclization of geranyl derivatives. The reaction of geranyl derivatives with N-bromosuccinimide (NBS) proceeds rapidly in CH2Cl2 to give the corresponding bromocyclization products in high yields as a ca. 1:1 mixture of endo- and exo-isomers. The reactivity of geranyl derivatives highly depends on the terminal substituent: electron-donating substituents increase the reactivity, while electron-withdrawing substituents decrease the reactivity.

    DOI: 10.1021/acs.orglett.9b00352

    Web of Science

    researchmap

  • 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

     More details

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

    researchmap

  • 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

     More details

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

    researchmap

  • 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

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    Densely functionalized tetrahydropyridines were stereoselectively synthesized from 1,6-dihydropyridines. Exploiting a carbonyl group installed at the C3 position of the 1,6-dihydropyridine system, we devised a strategy for cyanomethylation at C2/C6 and subsequent divergent installation of an allyl group at C3/C5 in a highly regio- and stereo-controlled manner. This versatile protocol for programmable functionalization of the 1,6-dihydropyridine system allows the divergent and streamlined synthesis of multiply-substituted tetrahydropyridines as an important class of biologically and medicinally relevant scaffolds. Two of the N-heterocyclic compounds bearing an alkyl nitrile group showed anti-hepatitis C virus (HCV) activity. (C) 2017 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmc.2017.03.011

    Web of Science

    researchmap

  • 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

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    A convergent coupling reaction is described that enables the stereoselective construction of angularly substituted trans-fused decalins from acyclic precursors. The process builds on our alkoxide-directed titanium-mediated alkyne-alkyne coupling and employs a 1,7-enyne coupling partner. Overall, the reaction is thought to proceed through initial formation of a tetrasusbstituted metallacyclopentadiene, stereoselective intramolecular [4+2] cycloaddition, elimination, isomerization, and regio- and stereoselective protonation. Distinct from our early studies directed at the synthesis of trans-fused hydrindanes, the current annulative coupling reveals an important effect of TMSCl in controlling the final protonation-the event that establishes the stereochemistry of the ring fusion.

    DOI: 10.1002/anie.201606962

    Web of Science

    researchmap

  • multipotent intermediate Reviewed

    Haruki Mizoguchi, Hiroki Oguri

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

     More details

    Language:Japanese  

    researchmap

  • 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

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    Investigation of titanium-centered metallacycle-mediated cross-coupling between unsymmetrical internal alkynes has led to the discovery that TMSCl significantly accelerates the C-C bond forming event. We report a collection of results that compare the efficiency of this reaction employing Ti(Oi-Pr)(4)/2n-BuLi in PhMe with and without TMSCl, demonstrating in every case that the presence of TMSCl has a profound impact on efficiency. While relevant in the context of developing this fundamental bond-forming process as an entry to more complex organometallic transformations, these modified reaction conditions allow coupling processes to be run at &gt;10 times the concentrations previously possible [in 2.4 M n-BuLi (hexanes)], without the requirement of additional solvent. Finally, we demonstrate the effectiveness of these modified reaction conditions for the annulative cross-coupling between TMS-alkynes and 1,6-enynes leading to the formation of angularly substituted hydrindanes with, now well appreciated, high levels of regio- and stereoselection. (C) 2016 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2016.07.045

    Web of Science

    researchmap

  • 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

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    LiOOt-Bu is an effective oxidant for converting the penultimate organometallic intermediate generated in a titanium alkoxide-mediated [2+2+2] reaction cascade to an allylic alcohol. Oxidation of the presumed allylic titanium species is highly regioselective, providing direct access to substituted hydrindanes containing a primary allylic alcohol. In addition to demonstrating the feasibility of this oxidation process, we document the ability to convert the primary allylic alcohol products to angularly substituted cis-fused hydrindanes. (C) 2015 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2015.01.029

    Web of Science

    researchmap

  • 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

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    Bridged bicyclic metallacyclopentenes generated from the [4 + 2] cycloaddition of metallacyclopentadienes with alkenes have been proposed as reactive intermediates in the course of [2 + 2 + 2] annulation reactions. Recently a collection of alkoxide-directed Ti-mediated [2 + 2 + 2] annulation reactions have been discovered for the synthesis of densely functionalized hydrindanes, where the bridged bicyclic metallacyclopentenes from intramolecular [4 + 2] were treated as fleeting intermediates en route to cyclohexadiene products formed by formal cheletropic extrusion of Ti(Oi-Pr)(2). In studies aimed at understanding the course of these organometallic cascade reactions it was later discovered that these bridged bicyclic intermediates can be trapped by various elimination processes. Here, we have realized metallacycle-mediated annulation reactions for the assembly of angularly substituted decalins-structural motifs that are ubiquitous in natural products and molecules of pharmaceutical relevance. In addition to defining the basic annulation reaction we have discovered a surprising stability associated with the complex organometallic intermediates generated in the course of this coupling process and document here the ability to control the fate of such species. Ligand-induced cheletropic extrusion of the titanium center delivers cyclohexadiene-containing products, while several distinct protonation events have been identified to realize polycyclic products that contain three new stereocenters (one of which is the angular quaternary center that is a hallmark of alkoxide-directed titanium-mediated [2 + 2 + 2] annulation reactions). Examples of this metallacycle-mediated annulation reaction are provided to demonstrate that a range of stereodefined fused bicyclo[4.4.0]decanes are accessible, including those that contain aromatic and aliphatic substituents, and an empirical model is presented to accompany the observations made.

    DOI: 10.1021/jacs.5b02107

    Web of Science

    researchmap

  • 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

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

    Copper-catalyzed 6-endo cyclization of N-propargylic beta-enaminocarbonyls was developed for the synthesis of oxidation-labile 1,6-dihydropyridines. This synthetic method allows flexible and regio-defined assembly of various substituents at the N1, C2, C3, C4, and C6 positions of 1,6-dihydropyridines under mild conditions.

    DOI: 10.1039/c5ob00356c

    Web of Science

    researchmap

  • 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

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    Angularly substituted trans-fused hydroindanes are now accessible by the direct and convergent union of trimethylsilyl (TMS)-alkynes with 4-hydroxy-1,6-enynes by a process that forges three C C bonds, one C H bond, and two new stereocenters. The annulation is proposed to proceed by initial formation of a Ti-alkyne complex (with a TMS-alkyne) followed by regioselective alkcodde-directed coupling with the enyne, stereoselective intramolecular cycloaddition, elimination of phenoxide, 1,3-metallotropic shift, and stereoselective protonation of the penultimate allylic organometallic intermediate. Several examples are given to demonstrate the compatibility of this reaction with substrates bearing aromatic and aliphatic substituents, and an empirical model is presented to accompany the stereochemical observations.

    DOI: 10.1021/ja504374j

    Web of Science

    researchmap

  • Biogenetically inspired synthesis and skeletal diversification of indole alkaloids Reviewed

    Haruki Mizoguchi, Hideaki Oikawa, Hiroki Oguri

    NATURE CHEMISTRY   6 ( 1 )   57 - 64   2014.1

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:NATURE PUBLISHING GROUP  

    To access architecturally complex natural products, chemists usually devise a customized synthetic strategy for constructing a single target skeleton. In contrast, biosynthetic assembly lines often employ divergent intramolecular cyclizations of a polyunsaturated common intermediate to produce diverse arrays of scaffolds. With the aim of integrating such biogenetic strategies, we show the development of an artificial divergent assembly line generating unprecedented numbers of scaffold variations of terpenoid indole alkaloids. This approach not only allows practical access to multipotent intermediates, but also enables systematic diversification of skeletal, stereochemical and functional group properties without structural simplification of naturally occurring alkaloids. Three distinct modes of [412] cyclizations and two types of redox-mediated annulations provided divergent access to five skeletally distinct scaffolds involving iboga-, aspidosperma-, andranginine- and ngouniensine-type skeletons and a non-natural variant within six to nine steps from tryptamine. The efficiency of our approach was demonstrated by successful total syntheses of (+/-)-vincadifformine, (+/-)-andranginine and (2)-catharanthine.

    DOI: 10.1038/NCHEM.1798

    Web of Science

    researchmap

  • 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

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:BEILSTEIN-INSTITUT  

    By emulating the universal biosynthetic strategy, which employs modular assembly and divergent cyclizations, we have developed a four-step synthetic process to yield a collection of natural-product-inspired scaffolds. Modular assembly of building blocks onto a piperidine-based manifold 6, having a carboxylic acid group, was achieved through Ugi condensation, N-acetoacetylation and diazotransfer, leading to cyclization precursors. The rhodium-catalyzed tandem cyclization and divergent cycloaddition gave rise to tetracyclic and hexacyclic scaffolds by the appropriate choice of dipolarophiles installed at modules 3 and 4. A different piperidine-based manifold 15 bearing an amino group was successfully applied to demonstrate the flexibility and scope of the unified four-step process for the generation of structural diversity in the fused scaffolds. Evaluation of in vitro antitrypanosomal activities of the collections and preliminary structure-activity relationship (SAR) studies were also undertaken.

    DOI: 10.3762/bjoc.8.105

    Web of Science

    researchmap

  • 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

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

    We have developed a unique catalytic protocol for direct gem-vinylation of tryptamine derivatives employing Hg(OTf)(2) as the optimum catalyst. The intermolecular vinylations with a series of aromatic acetylenes proceeded under ambient temperature at the C2 positions of indoles with high functional group tolerance. Based on the mechanistic insights, we further developed the tandem reactions successfully constructing a quaternary center.

    DOI: 10.1039/c2ob25236h

    Web of Science

    researchmap

  • 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

     More details

    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

    CiNii Article

    CiNii Books

    researchmap

  • 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

     More details

    Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    We report the development of a divergent synthetic process entailing four-step access to the elaborate fused skeletons reminiscent of aspidophytines and transtaganolides. A variety of branched precursors were synthesized on the basis of Ugl condensations and installation of diazoimide and subjected to rhodium-catalyzed tandem reactions. Switching of cyclization modes was demonstrated by the choice of the amine building blocks installed at site C.

    DOI: 10.1021/ol901020a

    Web of Science

    researchmap

▼display all

MISC

  • 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

     More details

    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

    researchmap

  • 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

     More details

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

    researchmap

  • 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

     More details

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

    researchmap

  • 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

     More details

    Language:English   Publishing type:Book review, literature introduction, etc.   Publisher:WILEY-V C H VERLAG GMBH  

    Alkoxide-directed metallacycle-mediated cross-coupling is a rapidly growing area of reaction methodology in organic chemistry. Over the last decade, developments have resulted in more than thirty new and highly selective intermolecular (or convergent) C-C bond-forming reactions that have established powerful retrosynthetic relationships in stereoselective synthesis. While early studies were focused on developing transformations that forge a single C-C bond by way of a functionalized and unsaturated metallacyclopentane intermediate, recent advances mark the ability to employ this organometallic intermediate in additional stereoselective transformations. Among these more advanced coupling processes, those that embrace the metallacycle in subsequent [4+2] chemistry have resulted in the realization of a number of highly selective annulative cross-coupling reactions that deliver densely functionalized and angularly substituted carbocycles. This review discusses the early development of this chemistry, recent advances in reaction methodology, and shares a glimpse of the power of these processes in natural product synthesis.

    DOI: 10.1002/ijch.201600098

    Web of Science

    researchmap

  • 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

     More details

    Language:Japanese   Publishing type:Book review, literature introduction, etc.   Publisher:SOC SYNTHETIC ORGANIC CHEM JPN  

    Polyoxygenated steroids cardenolides, typified by ouabagenin, possess a broad spectrum of biological activity such as inotropic activity. Due to their unique structure, including unusual cis-fused A/B- and C/D ring junction, and a number of beta-configured oxygenated functional group, they have been an attractive target in chemical synthesis. In this review, recent developments in the practical synthetic strategies toward these cardenolides are described.

    DOI: 10.5059/yukigoseikyokaishi.75.253

    Web of Science

    researchmap

  • 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

     More details

    Language:Japanese   Publishing type:Book review, literature introduction, etc.   Publisher:SOC SYNTHETIC ORGANIC CHEM JPN  

    With intention to formulate a potentially general synthetic strategy generating a collection of skeletally diverse scaffolds without simplifying a structural feature of natural products, we devised an artificial assembly line of terpenoid indole alkaloids and its variants. Inspired by the key biosynthetic intermediate, dehydrosecodine, responsible for divergent intramolecular cyclizations, a "multipotent intermediate" with improved stability and versatile reactivity was designed to establish a streamlined divergent synthetic process. A newly developed copper-catalyzed cyclization protocol allowed rapid formation of the sensitive dihydropyridine system. By harnessing the versatile reactivity of the multipotent intermediate, three types of bioinspired [4+2] cycloadditions as well as two types of oxidation-triggered cyclizations were successfully implemented to generate five distinct scaffolds involving iboga-, aspidosperma-, andranginine- and ngouniensine-type skeletons and unnatural tetracyclic framework within 6-9 steps from tryptamine. Furthermore, simple manipulations of the [4+2] products allowed total synthesis of (-)-catharanthine, (+/-)-vincadifformine and (+/-)-andranginine, demonstrating a structural relevance of our compound collections to the natural products.

    DOI: 10.5059/yukigoseikyokaishi.74.854

    Web of Science

    researchmap

  • 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

     More details

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

    DOI: 10.1271/kagakutoseibutsu.53.345

    researchmap

  • 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   12 - 17   2014.5

     More details

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

    researchmap

▼display all

Presentations

  • 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 

     More details

    Language:Japanese  

    researchmap

  • 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 

     More details

    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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    researchmap

  • 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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    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 

     More details

    Language:English   Presentation type:Oral presentation (general)  

    researchmap

  • Metallacycle-mediated synthesis of highly functionalized decalins International conference

    Haruki Mizoguchi, Glenn C. Micalizio

    National Organic Symposium 2017  2017 

     More details

    Language:English   Presentation type:Poster presentation  

    researchmap

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

    Haruki Mizoguchi, Hideaki Oikawa, Hiroki Oguri

    ACS 250th National Meeting, Boston, MA  2015 

     More details

    Language:English   Presentation type:Poster presentation  

    researchmap

  • Metallacycle-mediated synthesis of highly functionalized decalins International conference

    Haruki Mizoguchi, Glenn C. Micalizio

    ACS 250th National Meeting, Boston, MA  2015 

     More details

    Language:English   Presentation type:Oral presentation (general)  

    researchmap

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

    Haruki Mizoguchi, Hideaki Oikawa, Hiroki Oguri

    REAXYS INSPIRING CHEMISTRY CONFERENCE 2014, Grindelwald  2014 

     More details

    Language:English   Presentation type:Poster presentation  

    researchmap

  • 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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    researchmap

  • 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 

     More details

    Language:English   Presentation type:Poster presentation  

    researchmap

  • 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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    researchmap

  • 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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    researchmap

  • 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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    researchmap

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

    Haruki Mizoguchi, Hiroki Oguri, Hideaki Oikawa

    11th iCeMS International Symposium  2011.12 

     More details

    Language:English   Presentation type:Poster presentation  

    researchmap

  • 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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    researchmap

  • 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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    researchmap

  • 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 

     More details

    Language:English   Presentation type:Poster presentation  

    researchmap

  • 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 

     More details

    Language:English   Presentation type:Oral presentation (general)  

    researchmap

  • 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 

     More details

    Language:Japanese   Presentation type:Poster presentation  

    researchmap

  • 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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    researchmap

  • 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 

     More details

    Language:Japanese   Presentation type:Poster presentation  

    researchmap

  • 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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    researchmap

  • 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 

     More details

    Language:Japanese   Presentation type:Oral presentation (general)  

    researchmap

▼display all

Awards

  • 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

     More details

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

    2018.7  

    MIZOGUCHI Haruki

     More details

  • 2014 Reaxys PhD Prize Finalist

    2014.9  

    MIZOGUCHI Haruki

     More details

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

    2012.11  

    MIZOGUCHI Haruki

     More details

  • Otsu Conference 2010 (Banyu Life Science Foundation International)

    2010.10  

    MIZOGUCHI Haruki

     More details

  • 22th Banyu Sapporo Symposium poster award

    2010.7  

    MIZOGUCHI Haruki

     More details

  • Hokkaido University Clark Award

    2008.3  

    MIZOGUCHI Haruki

     More details

▼display all

Research Projects

  • 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

      More details

    Authorship:Principal investigator 

    researchmap

  • 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

      More details

    Authorship:Principal investigator 

    researchmap

  • 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

      More details

    Authorship:Principal investigator 

    researchmap

  • 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

      More details

    Authorship:Principal investigator 

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

    researchmap

  • 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

      More details

    Authorship:Principal investigator 

    researchmap

  • 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

      More details

    Authorship:Principal investigator 

    researchmap

  • 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

      More details

    Authorship:Principal investigator  Grant type:Competitive

    researchmap

  • 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

      More details

    Authorship:Principal investigator  Grant type:Competitive

    researchmap

  • 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

      More details

    Authorship:Principal investigator  Grant type:Competitive

    researchmap

  • 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

      More details

    Authorship:Principal investigator  Grant type:Competitive

    researchmap

  • 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

      More details

    Authorship:Principal investigator  Grant type:Competitive

    researchmap

  • 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

      More details

    Authorship:Principal investigator  Grant type:Competitive

    researchmap

  • 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

      More details

    Authorship:Principal investigator  Grant type:Competitive

    researchmap

▼display all

 

Class subject in charge

  • 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

▼display all