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Efficient synthesis of natulally occurring middle molecular compounds

Planned Research

Project AreaMiddle molecular strategy: Creation of higher bio-functional molecules by integrated synthesis.
Project/Area Number 15H05842
Research Category

Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionHokkaido University

Principal Investigator

TANINO Keiji  北海道大学, 理学研究院, 教授 (40217146)

Project Period (FY) 2015-06-29 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥45,500,000 (Direct Cost: ¥35,000,000、Indirect Cost: ¥10,500,000)
Fiscal Year 2019: ¥8,840,000 (Direct Cost: ¥6,800,000、Indirect Cost: ¥2,040,000)
Fiscal Year 2018: ¥8,840,000 (Direct Cost: ¥6,800,000、Indirect Cost: ¥2,040,000)
Fiscal Year 2017: ¥8,840,000 (Direct Cost: ¥6,800,000、Indirect Cost: ¥2,040,000)
Fiscal Year 2016: ¥8,840,000 (Direct Cost: ¥6,800,000、Indirect Cost: ¥2,040,000)
Fiscal Year 2015: ¥10,140,000 (Direct Cost: ¥7,800,000、Indirect Cost: ¥2,340,000)
Keywords合成化学 / 生物機能分子 / フローケミストリー / ソラノエクレピン / シストセンチュウ / ブラシリカルジン
Outline of Final Research Achievements

The aim of this work is the development of powerful methods for the synthesis of middle molecular compounds such as solanoeclepin A. Solanoeclepin A has been considered as the key material for exterminating potato cyst nematode, a pest which gives destructive damage to the production of potatoes. We found a practical method for providing a key intermediate of the total synthesis of solanoeclepin A by the use of a flow chemistry. Another important achievement in this work is the total synthesis of brasilicardins. The middle molecular natural compound, which exhibits a potent immunosuppressive activity, consisting of a terpenoid skeleton with an amino acid moiety and sugar units.

Academic Significance and Societal Importance of the Research Achievements

天然有機化合物の中には、医薬や農薬としての需要がありながら、天然資源からの供給が困難なものが存在する。有機化学の進歩により、人工合成品として供給される化合物がある一方で、複雑な分子構造を持つ中分子化合物には合成困難なものが多く残されている。
本研究の目的は、反応集積化(フロー合成法)など最先端の手法を導入してこの限界を打破し、ソラノエクレピンAに代表される社会的要請の高い超微量天然中分子の高効率合成を達成することにある。ソラノエクレピンAは、世界的な食料生産上の大害虫ジャガイモシストセンチュウを根絶に追い込むための鍵物質とされ、農業分野での実用化が期待されている化合物である。

Report

(6 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • Research Products

    (40 results)

All 2020 2019 2018 2017 2016 2015

All Journal Article (20 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 20 results,  Open Access: 5 results,  Acknowledgement Compliant: 7 results) Presentation (17 results) (of which Int'l Joint Research: 7 results,  Invited: 16 results) Book (1 results) Patent(Industrial Property Rights) (1 results) Funded Workshop (1 results)

  • [Journal Article] Development of a 1,3a,6a-Triazapentalene Derivative as a Compact and Thiol-specific Fluorescent Labeling Reagent2020

    • Author(s)
      Atsushi Nakayama, Akira Otani, Tsubasa Inokuma, Daisuke Tsuji, Haruka Mukaiyama, Akira Nakayama, Kohji Itoh, Akira Otaka, Keiji Tanino, and Kosuke Namba
    • Journal Title

      Communications Chemistry

      Volume: 3 Issue: 1 Pages: 1-9

    • DOI

      10.1038/s42004-019-0250-0

    • NAID

      120006877882

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Inhibition of Lipid Droplet Formation by Ser/Thr Protein Phosphatase PPM1D Inhibitor, SL-1762019

    • Author(s)
      Rui Kamada, Nozomi Kimura, Fumihiko Yoshimura, Keiji Tanino, and Kazuyasu Sakaguchi
    • Journal Title

      Pros One

      Volume: 14 Issue: 2 Pages: e0212682-e0212682

    • DOI

      10.1371/journal.pone.0212682

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Asymmetric Total Synthesis of Laurallene2019

    • Author(s)
      Yoshimura Fumihiko、Okada Taku、Tanino Keiji
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 2 Pages: 559-562

    • DOI

      10.1021/acs.orglett.8b03889

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic study of andrastins: stereoselective construction of the BCD-ring system2019

    • Author(s)
      Yoshimura Fumihiko、Abe Taiki、Ishioka Yuichi、Tanino Keiji
    • Journal Title

      The Journal of Antibiotics

      Volume: 72 Issue: 6 Pages: 384-388

    • DOI

      10.1038/s41429-018-0136-x

    • NAID

      120006651803

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An Intermolecular [4+3] Cycloaddition Reaction Using 3-Hydroxy-2-pyrone Derivatives with an Oxyallyl Cation2019

    • Author(s)
      Takahiro Suzuki, Takamune Yanagisawa, and Keiji Tanino
    • Journal Title

      Heterocycles

      Volume: 99 Issue: 2 Pages: 848-855

    • DOI

      10.3987/com-18-s(f)79

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Substituted Cyclopentenol Derivatives via Intramolecular Addition Reaction of Vinylcopper Species2019

    • Author(s)
      Hideomi Yamaga and Keiji Tanino
    • Journal Title

      Synlett

      Volume: 30 Issue: 02 Pages: 230-234

    • DOI

      10.1055/s-0037-1611366

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Total Synthesis of Brasilicardins2018

    • Author(s)
      Yoshimura Fumihiko、Itoh Ryusei、Torizuka Makoto、Mori Genki、Tanino Keiji
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 57 Issue: 52 Pages: 17161-17167

    • DOI

      10.1002/anie.201811403

    • NAID

      120006775546

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Total Synthesis of (-)-Maldoxin, a Common Biosynthetic Ancestor of the Chloropupukeananin Family2018

    • Author(s)
      Takahiro Suzuki, Soichiro Watanabe, Muhammet Uyanik, Kazuaki Ishihara, Susumu Kobayashi, and Keiji Tanino
    • Journal Title

      Org. Lett.

      Volume: 20 Issue: 13 Pages: 3919-3922

    • DOI

      10.1021/acs.orglett.8b01502

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Enantioselective Total Synthesis of (+)-Iso-A82775C, a Proposed Biosynthetic Precursor of Chloropupukeananin2017

    • Author(s)
      Suzuki Takahiro、Watanabe Soichiro、Kobayashi Susumu、Tanino Keiji
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 4 Pages: 922-925

    • DOI

      10.1021/acs.orglett.7b00085

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nucleophilic Addition of Alkanenitriles to Aldehydes via N-Silyl Ketene Imines Generated In Situ2017

    • Author(s)
      Yoshimura Fumihiko、Tanino Keiji、Saito Hiroki、Abe Taiki
    • Journal Title

      Synlett

      Volume: 28 Issue: 14 Pages: 1816-1820

    • DOI

      10.1055/s-0036-1588424

    • NAID

      120006502485

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Inhibition of Ser/Thr phosphatase PPM1D induces neutrophil differentiation in HL-60 cells2017

    • Author(s)
      Kamada Rui、Kudoh Fuki、Yoshimura Fumihiko、Tanino Keiji、Sakaguchi Kazuyasu
    • Journal Title

      The Journal of Biochemistry

      Volume: 162 Pages: 303-308

    • DOI

      10.1093/jb/mvx032

    • NAID

      40021380581

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Construction of Bicyclic Systems Containing an Oxygen Bridge by Isomerization of Cyclic Epoxy Alcohols2017

    • Author(s)
      Masaru Iwakura, Hiroshi Tokura, and Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 12 Pages: 1223-1226

    • DOI

      10.1016/j.tetlet.2017.02.023

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthetic Studies on Psiguadial B: Construction of Bicyclo[4.3.1]decane Skeleton via Double Cyclization Reaction of Alkyne Dicobalt Complex2017

    • Author(s)
      Masahiko Kinebuchi, Ryohei Uematsu, and Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 14 Pages: 1382-1386

    • DOI

      10.1016/j.tetlet.2017.02.058

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Non-reductive Decyanation Reactions of Disubstituted Malononitrile Derivatives Promoted by NaHMDS2017

    • Author(s)
      Daisuke Domon, Masaru Iwakura, and Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 20 Pages: 1957-1960

    • DOI

      10.1016/j.tetlet.2017.04.012

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthetic Studies on Enfumafungin: Stereoselective Synthesis of the CD Ring Segment2016

    • Author(s)
      Manabu Fujitani and Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 57 Issue: 43 Pages: 4838-4841

    • DOI

      10.1016/j.tetlet.2016.09.057

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthetic Studies on Azadirachtin: Construction of the ABC Ring System via the Diels-Alder Reaction of a Vinyl Allenylsilane Derivative2015

    • Author(s)
      Kentaro Sakurai and Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 56 Issue: 3 Pages: 496-499

    • DOI

      10.1016/j.tetlet.2014.12.062

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of yellow and red fluorescent 1,3a,6a-triazapentalenes and the theoretical investigation of their optical properties2015

    • Author(s)
      Kosuke Namba, Ayumi Osawa, Akira Nakayama, Akane Mera, Fumi Tano, Yoshiro Chuman, Eri Sakuda, Tetsuya Taketsugu, Kazuyasu Sakaguchi, Noboru Kitamura, Keiji Tanino
    • Journal Title

      Chemical Science

      Volume: 6 Issue: 2 Pages: 1083-1093

    • DOI

      10.1039/c4sc02780a

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Acid-catalyzed [4+3] cycloaddition reaction of N-nosyl pyrroles2015

    • Author(s)
      Shibata, M.; Fuchigami, R.; Kotaka, R.; Namba, K.; Tanino, K
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 26-27 Pages: 4495-4499

    • DOI

      10.1016/j.tet.2015.02.071

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Novel Inhibitors Targeting PPM1D Phosphatase Potently Suppress Cancer Cell Proliferation.2015

    • Author(s)
      Ogasawara, S., Kiyota, Y., Chuman, Y., Kowata, A., Yoshimura, F., Tanino, K., Kamada, R., and Sakaguchi, K.
    • Journal Title

      Bioorg. Med. Chem.

      Volume: 23 Issue: 19 Pages: 6246-6249

    • DOI

      10.1016/j.bmc.2015.08.042

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Total Synthesis of Palau’amine2015

    • Author(s)
      K. Namba, K. Takeuchi, Y. Kaihara, M. Oda, A. Nakayama, A. Nakayama, M. Yoshida, and K. Tanino
    • Journal Title

      Nature Communications

      Volume: 6 Issue: 1 Pages: 8731-8731

    • DOI

      10.1038/ncomms9731

    • NAID

      120006999407

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] Natural Product Synthesis Based on Cyclization Reactions of Nitriles2019

    • Author(s)
      Keiji Tanino
    • Organizer
      The 8th Japanese-Sino Symposium on Organic Chemistry for Young Scientists
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] シアノ基の特性を活用した天然物合成2019

    • Author(s)
      谷野圭持
    • Organizer
      名古屋大学第111回創薬科学セミナー
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 超微量生物機能性天然中分子の高効率合成2019

    • Author(s)
      谷野圭持
    • Organizer
      第9回CSJ化学フェスタ2019
    • Related Report
      2019 Annual Research Report
  • [Presentation] Total Synthesis of Natural Products Based on Cyclization Reactions of Nitriles2019

    • Author(s)
      Keiji Tanino
    • Organizer
      Hokkaido University & Peking University Joint Symposium 2019
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 多環性天然物ソラノエクレピンAの不斉全合成2018

    • Author(s)
      谷野 圭持
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] シアノ基の特性を活用した炭素-炭素結合形成法の開発2017

    • Author(s)
      谷野 圭持
    • Organizer
      平成29年度前期(春季)有機合成化学講習会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] シアノ基の特性を活用した天然物合成2017

    • Author(s)
      谷野 圭持
    • Organizer
      第52回天然物化学談話会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] シストセンチュウふ化促進物質の化学合成2017

    • Author(s)
      谷野 圭持
    • Organizer
      近畿化学協会合成部会フロー・マイクロ合成研究会 第31回公開講演会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] ふ化促進物質の全合成とジャガイモシストセンチュウ類防除へ向けた実用化研究2017

    • Author(s)
      谷野 圭持
    • Organizer
      日本線虫学会第25回大会(札幌大会)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 有機合成の力で天然物を新世代の農薬にする2017

    • Author(s)
      谷野 圭持
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Natural Product Synthesis by Utilizing the Cascade Reactions of Alkyne Dicobalt Complexes2016

    • Author(s)
      Keiji Tanino
    • Organizer
      The 10th International Symposium on Integrated Synthesis
    • Place of Presentation
      淡路夢舞台国際会議場(兵庫県・淡路市)
    • Year and Date
      2016-11-18
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] シストセンチュウふ化促進物質の全合成2016

    • Author(s)
      谷野圭持
    • Organizer
      第31回農薬デザイン研究会
    • Place of Presentation
      京都大学芝蘭会館(京都府・京都市)
    • Year and Date
      2016-11-17
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 全合成の現場から:誰のための反応開発か?2016

    • Author(s)
      谷野圭持
    • Organizer
      第42回反応と合成の進歩シンポジウム
    • Place of Presentation
      清水文化会館マリナート(静岡県・静岡市)
    • Year and Date
      2016-11-08
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Total Synthesis of Complex Polycyclic Natural Compounds2016

    • Author(s)
      Keiji Tanino
    • Organizer
      Peking University & Hokkaido University Joint Seminar on Organic Chemistry and Chemical Biology
    • Place of Presentation
      北京(中国)
    • Year and Date
      2016-05-26
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Total Synthesis of Complex Polycyclic Natural Compounds2016

    • Author(s)
      Keiji Tanino
    • Organizer
      The 12th International Symposium on Organic Reactions
    • Place of Presentation
      京都テルサ(京都府・京都市)
    • Year and Date
      2016-04-22
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Asymmetric Total Synthesis of Complex Polycyclic Natural Products2015

    • Author(s)
      Keiji Tanino
    • Organizer
      The 25th Symposium on Optically Active Compounds
    • Place of Presentation
      日本薬学会館長井ホール(東京都・渋谷区)
    • Year and Date
      2015-11-27
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Total Synthesis of Complex Polycyclic Natural Products2015

    • Author(s)
      Keiji Tanino
    • Organizer
      The 3rd International Symposium on Ambitious Leader’s Program Fostering Future Leaders to Open New Frontiers in Material Science
    • Place of Presentation
      北海道大学鈴木ホール(北海道・札幌市)
    • Year and Date
      2015-11-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Book] 天然有機化合物の全合成2018

    • Author(s)
      日本化学会
    • Total Pages
      208
    • Publisher
      化学同人
    • ISBN
      9784759813876
    • Related Report
      2017 Annual Research Report
  • [Patent(Industrial Property Rights)] PPM1D阻害剤2020

    • Inventor(s)
      坂口和靖,谷野圭持,他7名
    • Industrial Property Rights Holder
      坂口和靖,谷野圭持,他7名
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2020-040300
    • Filing Date
      2020
    • Related Report
      2019 Annual Research Report
  • [Funded Workshop] The 2nd International Symposium on Middle Molecular Strategy for Young Scientists2019

    • Related Report
      2019 Annual Research Report

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Published: 2015-07-02   Modified: 2022-11-04  

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