Grant-in-Aid for Scientific Research on Innovative Areas FY2017-2021Hybrid Catalysis

Masayuki Inoue » Japanese

Affiliation Graduate School of Pharmaceutical Sciences, The University of Tokyo
Position Professor
HP http://www.f.u-tokyo.ac.jp/~inoue/e_index.html
Speciality natural product synthesis, bioorganic chemistry
Keyword total synthesis, natural products, radical reactions, C-C coupling, biological activity
Institute The Pharmaceutical Society of Japan, The Chemical Society of Japan, The Society of Synthetic Organic Chemistry, Japan, American Chemical Society, Royal Society of Chemistry

Abstract

Natural products have been tremendously important in biology and human medicine because of their ability to modulate signal transductions in biological systems. Our research group focuses on development of new strategies for assembling the complex natural products in a concise fashion. To minimize number of steps and maximize convergency, we will explore and develop hybrid catalysis-mediated multi-component coupling reactions. Then, we will apply these reactions for efficient construction of a diverse collection of densely functionalized molecules, including anticancer natural product taxol.

Achievement

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Original papers

  • "Installation of O-Heterocycles to N-Heteroarenes via an Et3B/O2-mediated Radical Reaction of a-Alkoxy and a-Alkoxyacyl Tellurides"
    Kuwana, D.; Ovadia, B.; Kamimura, D.; Nagatomo, M.; *Inoue M.
    Asian J. Org. Chem.,2019, 8, XX-XX
  • "Construction of a 6/5/9-membered Tricyclic Structure of Cladiellins via Radical-polar Crossover Reaction"
    Nagatomo, M.; Fujimoto, Y.; Masuda, K.; *Inoue M.
    J. Antibiot.,2019
  • "Convergent Synthesis of Taxol Skeleton via Decarbonylative Radical Coupling Reaction"
    Matoba, H.; Watanabe, T.; Nagatomo, M.; *Inoue M.
    Org. Lett.,2018, 20, 7554-7557
  • "Convergent Total Synthesis of Asimicin via Decarbonylative Radical Dimerization"
    Kawamata, T.; Yamaguchi, A.; Nagatomo, M.; *Inoue M.
    Chem. Eur. J.,2018, 24, 18907 -18912
  • "Total Synthesis and Biological Evaluation of 19-Hydroxysarmentogenin-3-O-a-L-rhamnoside, Trewianin, and Their Aglycons"
    Urabe, D.; Nakagawa, Y.; Mukai, K.; Fukushima, K.; Aoki, N.; Itoh, H.; Nagatomo, M.; *Inoue, M.
    J. Org. Chem.,2018, 83, 13888-13910
  • "Target Identification of Yaku’amide B and Its Two Distinct Activities against Mitochondrial FoF1-ATP Synthase"
    Kitamura, K.; Itoh, H.; Sakurai, K.; Dan, S.; *Inoue M.
    J. Am. Chem. Soc.,2018, 140, 12189-12199
  • "Construction of a Pentacyclic Ring System of Isoryanodane Diterpenoids by SmI2-mediated Transannular Cyclization"
    Koshimizu, M.; Nagatomo, M.; *Inoue, M.
    Tetrahedron,2018, 74, 3384-3390
  • "A Three-Component Coupling Approach to the ACE-Ring Substructure of C19-Diterpene Alkaloids"
    Minagawa, K.; Urabe, D.; *Inoue, M.
    J. Antibiot.,2018, 71, 326-332
  • "Synthesis of the Tetracyclic Structure of Batrachotoxin Enabled by Bridgehead Radical Coupling and Pd/Ni-Promoted Ullmann Reaction"
    Sakata, K.; Wang, Y.; Urabe, D.; *Inoue, M.
    Org. Lett.,2018, 20, 130-133
  • "Total Synthesis of Resiniferatoxin Enabled by Radical-Mediated Three-Component Coupling and 7-endo Cyclization"
    Hashimoto, S.; Katoh, S.; Kato, T.; Urabe, D.; *Inoue, M.
    J. Am. Chem. Soc.,2017, 139, 16420-16429
  • "Unified Total Synthesis of Polyoxin J, L, and Fluorinated Analogues on the Basis of Decarbonylative Radical Coupling Reactions"
    Fujino, H.; Nagatomo, M.; Paudel, A.; Panthee, S.; Hamamoto, H.; Sekimizu, K.; *Inoue, M.
    Angew. Chem., Int. Ed.,2017, 56, 11865-11869

Review

  • 「Comprehensive Structure-Activity Relationship Studies of Macrocyclic Natural Products Enabled by Their Total Syntheses」 Itoh, H.; *Inoue M., Chem. Rev., 119, XX-XX,2019

Conference

  • Pharmaron Lecture, Peking University Shenzhen Graduate School
    "Total Synthesis and Biological Evaluation of Complex Natural Products", 招待講演
    Inoue, M.
    4/19/2019, Shenzhen, China
  • Southern University of Science and Technology
    "Radical-Based Approach for Synthesis of Complex Natural Products", 招待講演
    Inoue, M.
    4/18/2019, Shenzhen, China
  • 6th UK-Japan Conference on Asymmetric Catalysis
    "Radical-Based Approach for Synthesis of Complex Natural Products", 招待講演
    Inoue, M.
    11/6/2018, Fukuoka, Japan
  • International Symposium on Frontiers of Natural and Biomimetic Drugs on “Natural Product Synthesis”
    "Radical-Based Approach for Synthesis of Complex Natural Products", 招待講演
    Inoue, M.
    10/18/2018, Beijing, China
  • 22nd International Conference on Organic Synthesis (22-ICOS)
    "Radical-Based Approach for Synthesis of Complex Natural Products", 招待講演
    Inoue, M.
    9/20/2018, Florence, Italy
  • 24th Conference on Isoprenoids
    "Radical-Based Approach for Synthesis of Complex Natural Products", 招待講演
    Inoue, M.
    9/11/2018, Białystok, Poland
  • 256th ACS National Meeting (JOC Lectureship)
    "Total Synthesis and Biological Evaluation of Peptide Natural Products", 招待講演
    Inoue, M.
    8/19/2018, Boston, USA
  • Novartis Lectureship
    "Radical-Based Approach for Synthesis of Complex Natural Products", 招待講演
    Inoue, M.
    6/21/2018, Toronto, Canada
  • Swiss Chemical Society Lectureship
    "Radical-Based Approach for Synthesis of Complex Natural Products", 招待講演
    Inoue, M.
    5/7/2018-5/15/2018, Zurich, Bern, Fribourg, Genève, Lausanne, Basel, Switzerland
  • ACP Lectureship, Department of Chemistry, National Tsing Hua University
    "Radical-Based Approach for Synthesis of Complex Natural Products", 招待講演
    Inoue, M.
    1/24/2018, Hsinchu, Taiwan
  • ACP Lectureship, Institute of Biotechnology and Pharmaceutical Research
    "Radical-Based Approach for Synthesis of Complex Natural Products", 招待講演
    Inoue, M.
    1/23/2018, Taipei, Taiwan
  • ACP Lectureship, Institute of Chemistry, Academia Sinica
    "Radical-Based Approach for Synthesis of Complex Natural Products", 招待講演
    Inoue, M.
    1/22/2018, Taipei, Taiwan

Award

  • 「The Journal of Organic Chemistry Outstanding Publication of the Year Award Lectureship」
    受賞者:Inoue, M.
    贈呈元:
    受賞日:
  • 「Swiss Chemical Society Lectureship Award 2017/2018」
    受賞者:Inoue, M
    贈呈元:
    受賞日:

Conference Management

  • 国際会議, Local Host, ACS on Campus, Tokyo, Japan, 6/15/2018