Grant-in-Aid for Scientific Research on Innovative AreasPrecise Formation of a Catalyst Having a Specified Field for Use in Extremely Difficult Substrate Conversion Reactions

Hidetoshi Tokuyama » Japanese

Affiliation Graduate School of Pharmaceutical Sciences, Tohoku University
Position Professor
HP http://www.pharm.tohoku.ac.jp/~seizou/index-e.html
Speciality Synthetic Organic Chemistry, Total Synthesis of Natural Products
Keyword organic transformations, oxidation, phthalocyanines, amino acid derivatives
Institute The Pharmaceutical Society of Japan, The Chemical Society of Japan, The Society of Synthetic Organic Chemistry Japan, The International Society of Heterocyclic Chemistry

Abstract

Development and application of environmentally benign oxidation process based on fine design of catalytic system using metal-phthalocyanine complexes

Achievement

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Original papers

  • "Total Synthesis of (+)-CC-1065 Utilizing Ring Expansion Reaction of Benzocyclobutenone Oxime Sulfonate"
    Imaizumi, T.; Yamashita, Y.; Nakazawa, Y.; Okano, K.; Sakata, J.; *Tokuyama, H.
    Org. Lett., 2019, 21, 6185-6189
  • "Fluorescent labeling method re-evaluates the intriguing thermoresponsive behavior of poly(acrylamide-co-acrylonitrile)s with upper critical solution temperatures"
    *Otsuka, C.; Wakahara, Y.; Okabe, K.; Sakata, J.; Okuyama, M.; Hayashi, A.; Tokuyama, H.; *Uchiyama, S.
    Macromolecules, 2019, 52, 7646-7660
  • "Construction of Indole Structure on Pyrroloindolines via AgNTf<sub>2</sub>-Mediated Amination/Cyclization Cascade: Application to Total Synthesis of (+)-Pestalazine B"
    Hakamata, H.; Ueda, H.; *Tokuyama, H.
    Org. Lett., 2019, 21, 4205-4209
  • "Synthesis of Propargylic Ethers by Gold-Mediated Reaction of Terminal Alkynes with Acetals"
    Furuta, M.; Sugiyama, K.; Yamaguchi, M.; Ueda, H.; *Tokuyama, H.
    Chem. Pharm. Bull., 2019, 67, 872-876
  • "Double Functionalization of Styrenes by Cu-mediated Assisted Tandem Catalysis"
    Kawauchi, D.; Ueda, H.; Tokuyama, H.
    Eur. J. Org. Chem., 2019, 15, 2056-2060
  • "Synthetic Studies Toward Isoschizogamine: Construction of Pentacyclic Core Structure"
    Sugimoto, K.; Fujiwara, H.; Takada, A.; Kim, D.-G.; Ueda, H.; *Tokuyama, H.
    Heterocycles, 2018, 97, 1028-1049
  • "A Cell‐Targeted Non‐Cytotoxic Fluorescent Nanogel Thermometer Created with an Imidazolium‐Containing Cationic Radical Initiator"
    *Uchiyama, S.; Tsuji, T.; Kawamoto, K.; Okano, K.; Fukatsu, E.; Noro, T.; Ikado, K.; Yamada, S.; Shibata, Y.; Hayashi, T.; Inada, N.; Kato, M.; Koizumi, H.; *Tokuyama, H.
    Angew. Chem. Int. Ed., 2018, 57, 5413-5417
  • "Cordybislactone, a Stereoisomer of the 14-Membered Bislactone Clonostachydiol, from the Hopper Pathogenic Fungus Cordyceps sp. BCC 49294: Revision of the Absolute Configuration of Clonostachydiol"
    Ojima,K.; Yangchum, A.; Laksanacharoen, P.; Tasanathai, K.; Thanakitpipattana, D.; Tokuyama, K.; Isaka, M.
    J. Antibiot., 2018, 71, 351
  • "Synthesis of 9,10-Diarylanthracenes via Mg(TMP)<sub>2</sub>·2LiCl-Mediated Benzyne Generation/[4+2] Cycloaddition and Deoxygenation of 9,10-Epoxyanthracene Intermediates"
    Miyamoto, N.; Nakazawa, Y.; Nakamura, T.; Okano, K.; Sato, S.; Sun, Z.; Isobe, H.; Tokuyama, H.
    Synlett, 2018, 29, 513
  • "AgNTf<sub>2</sub>-Mediated Allylation with Allylsilanes at C3a-Position of Hexahydropyrroloindoles: Application to Total Syntheses of Amauromine Alkaloids"
    Hakamata, H.; Sato, S.; Ueda, H.; Tokuyama, H.
    Org. Lett., 2017, 19, 5308
  • "Total Synthesis of Actinophyllic Acid"
    Yoshii, Y.; Tokuyama, H.; Chen, D. Y.-K.
    Angew. Chem. Int. Ed., 2017, 56, 12277
  • "AgNTf2-Mediated Arylation of Bromopyrroloindolines"
    Sato, S.; Hirayama, A.; Adachi, T.; Kawauchi, D.; Ueda, H.; Tokuyama, H.
    Heterocycles, 2017, 94(10), 1940
  • "Total Syntheses of (+)-T988 B and C via AgNTf2-Mediated Coupling of Bromopyrroloindoline with Indole"
    Sato, S.; Hirayama, A.; Ueda, H.; Tokuyama, H.
    Asian J. Org. Chem., 2017, 6, 54-58
  • "Convergent Synthesis of 2-Aryl-Substituted Quinolines by Gold-Catalyzed Cascade Reaction"
    Ueda, H.; Yamaguchi, M.; Tokuyama, H.
    Chemical and Pharmaceutical Bulletin, 2016, 64, 824-829
  • "Conversion of Vindoline into 11-Mesyloxytabersonine"
    Han-ya, Y.; Inui, T.; Yokoshima, S.; Tokuyama, H.; Fukuyama, T.
    Chemical and Pharmaceutical Bulletin, 2016, 64, 800-804
  • "Structural determination of (–)-SCH 64874 and hirsutellomycin by semi-synthesis"
    Tokuyama, H.; Yamada, K.; Fujiwara, H.; Sakata, J.; Okano, K.; Sappan, M.; Isaka, M.
    The Journal of Organic Chemistry, 2017, 82, 353-371
  • "Condensation of Carboxylic Acids with Non-Nucleophilic N-Heterocycles and Anilides Using Boc2O"
    Umehara, A.; Ueda, H.; Tokuyama, H.
    The Journal of Organic Chemistry, 2016, 81, 11444-11453-
  • "An obtuse-angled corner unit for fluctuating carbon nanohoops"
    Sun, Z.; Miyamoto, N.; Sato, S.; Tokuyama, H.; Isobe, H.
    Chemistry-An Asian Journal, 2017, 12, 271-275
  • "Total Synthesis of (−)-Histrionicotoxin through a Stereoselective Radical Translocation–Cyclization Reaction"
    Sato, M.; Azuma, H.; Daigaku, A.; Sato, S.; Takasu, K.; Okano, K.; Tokuyama, H.
    Angewandte Chemie International Edition, 2017, 56, 1087-1091
  • "Bioinspired Total Synthesis of the Dimeric Indole Alkaloid (+)-Haplophytine by Direct Coupling and Late-Stage Oxidative Rearrangement"
    Satoh, H.; Ojima, K.; Ueda, H.; Tokuyama, H.
    Angewandte Chemie International Edition, 2016, 55, 15157-15161

Books

  • 「Recent Progress on the Total Synthesis of Duocarmycins A and SA, Yatakemycin, and PDE-I and PDE-II」
    Sakata, J.; *Tokuyama, H.
    「Cutting-Edge Organic Synthesis and Chemical Biology of Bioactive Molecules」,Yuichi Kobayashi, Springer Nature Singapore Pte Ltd, 2019, 101-124

Conference

  • The 18th Asian Chemical Congress
    "Development of Novel Indole Synthesis via Ring Expansion Reaction of Benzocyclobutenone Oxime Sulfonate:Its Application to Alkaloid Synthesis", Poster Presentation
    Sakata, J.; Yamashita, Y.; Imaizumi, T.; Tokuyama, H.
    12/8/2019~12/12/2019, Taipei, Taiwan
  • The 14th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-14)
    "Ring Expansion Reaction of Cyclic Ketoximes and Its Application to Total Synthesis of Alkaloids", Poster Presentation
    Tokuyama, H.
    9/26/2019~9/29/2019, Niseko, Japan
  • The 27th International Society of Heterocyclic Chemistry Congress
    "Total Synthesis of (–)–Dehydrobatzalladine C via Construction of Pyrrolopyrimidine Skeleton by Gold-Catalyzed Tandem Cyclization", Oral Presentation
    Itagaki, D.; Marumo, K.; Ueda, H.; Tokuyama, H.
    9/1/2019~9/6/2020, Kyoto, Japan
  • The 27th International Society of Heterocyclic Chemistry Congress
    "Total Synthesis of (+)-CC1065 via Two Directional Double Ring Expansion of Benzo-bis-Cyclobutenone Oxime Sulfonate", Poster Presentation
    Sakata, J.; Imaizumi, T.; Yamashita, Y.; Tokuyama, H.
    9/1/2019~9/7/2019, Kyoto, Japan
  • The 27th International Society of Heterocyclic Chemistry Congress
    "Total Synthesis of (–)-Deoxoapodine", Oral Presentation
    Okada, K.; Yoshida, K.; Ueda, H.; Tokuyama, H.
    9/1/2019~9/6/2019, Kyoto, Japan
  • The 47th Naito Conference C-H Bond Activation and Transformation
    "Synthetic Studies on Alkaloids utilizing C-H Functionalization", Invited Lecture
    Tokuyama, H.
    7/2/2019~7/5/2019, Sapporo, Japan
  • Tohoku University's Chemistry Summer School 2019
    "Development of Novel Indole Synthesis via Ring Expansion Reaction of Oxime Sulfonate: Its Application to Total Synthesis of (+)-CC-1065 and Isobatzellines ", Oral Presentation
    Yamashita, Y.; Imaizumi, T.; Poignant, L.; Sakata, J.; Tokuyama, H.
    6/20/2019~6/21/2019, Sendai, Japan
  • The 7th Georgian Bay International Conference on Bioinorganic Chemistry
    "Aerobic oxidative functionalization of organic molecules catalyzed by iron phathalocyanine complex", Invited Lecture
    Tokuyama, H.
    5/21/2019~5/25/2019, Parry Sound, Ontario, Canada
  • Sichuan University-Tohoku University Joint Symposium
    "otal Synthesis of Complex Alkaloids via a Late-Stage Functionalization Strategy", Invited Lecture
    Tokuyama, H.
    5/3/2019~5/6/2019, Chengdu, China
  • Let’s Leap ! Challenges in Organic Chemistry
    "Synthetic Strategies directed toward Next Generation Total Synthesis of Natural Products", Invited Lecture
    Tokuyama, H.
    4/20/2019~4/20/2019, Tokyo, Japan
  • The 14th International Kyoto Conference on New Aspects of Organic Chemistry
    "Development of AgNTf2-Mediated Amination/Cyclization Cascade and Application to Total Synthesis of (+)-Pestalazine B", Poster Presentation
    Hiroyuki Hakamata, Hirofumi Ueda, Hidetoshi Tokuyama
    11/12/2018~11/16/2018, Kyoto, Japan
  • The 13th International Conference on Cutting-Edge Organic Chemistry in Asia
    "Total Syntheses of Diketopiperazine Alkaloids", Poster Presentation
    Tokuyama, H.
    11/1/2018~11/4/2018, Bangkok, Thailand
  • International Congress on Pure & Applied Chemistry 2018
    "AgNTf<sub>2</sub>-Mediated Amination/Cyclization Cascade and Application to Total Synthesis of (+)-Pestalazine B", Invited Lecture
    Tokuyama, H.
    10/30/2018~11/2/2018, Langkawi, Malaysia
  • The 4th International Symposium on C-H Activation (ISCHA4)
    "Total Synthesis of (–)-Isoschizogamine via the Late-Stage C-H Functionalization", Invited Lecture
    Tokuyama, H.; Takada, A.; Fujiwara, H.; Sugimoto, K.; Ueda, H.
    8/30/2018~9/2/2018, Yokohama, Japan
  • The 11th International Symposium on Integrated Synthesis (ISONIS-11) and The 3rd International Symposium on Middle Molecular Strategy (ISMMS-3)
    "AgNTf<sub>2</sub>-Mediated Functionalization of Pyrroloindoles and Application to Synthesis of Natural Products", Poster Presentation
    Hakamata, H.; Sato, S.; Ueda, H.; Tokuyama, H.
    11/15/2017~11/17/2017, Awaji, Hyogo, Japan
  • The 26th International Society of Heterocyclic Chemistry Congress
    "Total Syntheses of (–)-Histrionicotoxin and (–)-Histrionicotocin 235A via Radical Translocation Cyclization Cascade", Oral Presentation
    Sato, M.; Azuma, H.; Daigaku, A.; Sato, S.; Takasu, K.; Okano, K.; Tokuyama, H.
    9/3/2017~9/8/2017, Regensburg, Germany
  • The International Symposium on Pure & Applied Chemistry (ISPAC) 2017
    "Total Synthesis of (–)-Histrionicotoxin via Radical Translocation-Cyclization Reaction", Keynote Lecture
    Tokuyama, H.
    6/8/2017~6/10/2017, Ho Chi Minh City, Vietnam
  • Quarter Century Anniversary Banyu Symposium
    "Total Synthesis of Dimeric Indole Alkaloids via Late-Stage Chemoselective Oxidation", Invited Lecture
    Tokuyama, H.
    12/3/2016~12/3/2016, Tokyo, Japan
  • The 10th International Symposium on Integrated Synthesis (ISONIS-10)
    "Tokuyama, H.; Satoh, H.; Ojima, K.; Ueda, H.", Poster Presentation
    Bio-inspired Total Synthesis of (+)-Haplophytine
    11/18/2016~11/19/2016, Awaji Island, Hyogo, Japan
  • ACP-2016-Korea ICCEOCA-11/ARNCEOCA-2
    "Total Synthesis of Dimeric Indole Alkaloids", Poster Presentation
    Ueda, H.; Satoh, H.; Ojima, K.; Sato, S.; Hirayama, A.; Tokuyama, H.
    10/27/2016~10/30/2016, Daejeon, Korea
  • Otsuka Organic Chemistry Symposium
    "Synthetic Studies on Architecturally Complex N-heterocyclic Natural Products", Invited Lecture
    Tokuyama, H.
    9/10/2016~9/11/2016, Tokushima, Japan
  • International Symposium on Pure & Applied Chemistry (ISPAC) 2016
    "Total Synthesis of Architecturally Complex N-Heterocyclic Natural Products", Invited Lecture
    Tokuyama, H.
    8/15/2016~8/20/2016, Kutching, Sarawak, Malaysia

Award

  • 「International Congress on Pure & Applied Chemistry 2018 Langkawi, Symposium Award」
    受賞者:Hidetoshi Tokuyama
    贈呈元:Institut Kimia Malaysia
    受賞日:11/1/2018
  • 「Lectureship Award (China)」
    受賞者:Hidetoshi Tokuyama
    贈呈元:The 12th International Conference on Cutting-Edge Organic Synthesis in Asia
    受賞日:11/5/2017

Media

  • Org. Lett. volum 21, Issue 16, August 16, 2019, カバーピクチャ
    Imaizumi, T.; Yamashita, Y.: Nakazawa, Y.; Okano, K.; Sakata, J.; Tokuyama, H., 8/16/2019
    PDF File
  • Angewandte Chemie International Edition, その他
    「Author Profile Hidetoshi Tokuyama」
    Hidetoshi Tokuyama, 1/8/2018
    PDF File