• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Construction of Medium-sized Carbocycles Based on Pericyclic Reactions: Application to Natural Product Synthesis

Research Project

Project/Area Number 21H01923
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionHokkaido University

Principal Investigator

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

Project Period (FY) 2021-04-01 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥16,900,000 (Direct Cost: ¥13,000,000、Indirect Cost: ¥3,900,000)
Fiscal Year 2023: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2022: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2021: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Keywordsペリ環状反応 / 中員環 / 天然物 / 全合成 / 高次構造 / 転位反応 / 高次構造天然物 / 電子環状反応 / 7員環 / 環化反応
Outline of Research at the Start

自然界には、様々な大きさの炭素環が互いに縮合した複雑な分子構造を持つ天然有機化合物が数多く存在する。それら天然物の化学合成は医薬品の開発にも繋がり、学術面のみならず社会的な要請にも応える重要な研究課題である。本研究では、独自に開発した有機合成反応を駆使し、従来の方法では困難な中員環炭素骨格構築法を開発する。さらに、天然物合成への応用を通して、その有用性を実証する。

Outline of Final Research Achievements

New methods for the construction of medium-sized carbocycles were developed based on pericyclic reactions. The 8pi-electrocyclic reaction of triene derivatives under basic conditions gave rise to seven-membered carbocycles. The utility of the new method was demonstrated through the concise total synthesis of 6,11-epoxyisodaucane, an essential oil constituent extracted from the Tritomaria polita liverwort.
On the other hand, the Cope rearrangement reaction of a five-membered gem-divinyl compound was developed for obtaining a nine-membered compound. The product was transformed into an analogue of Cristaxenicin A, a natural product having a unique core structure consisting of a nine-membered carbocycle coupled with a substituted dihydropyran.

Academic Significance and Societal Importance of the Research Achievements

天然物の全合成研究は、新しい合成手法の開発を促し、有機化学の飛躍的な発展をもたらしてきた。その意義は学術面に留まらず、医薬や農薬の創出など社会的な要請にも応えるものである。
本研究では、新たに7から9員環までの大きさをもつ炭素環の効率的な構築法を開発し、それら新手法の有用性を天然物の全合成において検証した。合成標的の一つであるCristaxenicin Aは、リーシュマニア症の原因原虫に対する抗原虫活性を示し、治療薬のリード化合物として期待される天然物である。

Report

(4 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Annual Research Report
  • 2021 Annual Research Report
  • Research Products

    (29 results)

All 2024 2023 2022 2021

All Journal Article (18 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 18 results,  Open Access: 4 results) Presentation (11 results) (of which Invited: 1 results)

  • [Journal Article] Alcohol synthesis based on the S<sub>N</sub>2 reactions of alkyl halides with the squarate dianion2024

    • Author(s)
      Sato Kazuto、Fujita Tomoyuki、Takeuchi Takashi、Suzuki Takahiro、Ikeuchi Kazutada、Tanino Keiji
    • Journal Title

      Organic &amp; Biomolecular Chemistry

      Volume: 22 Issue: 7 Pages: 1369-1373

    • DOI

      10.1039/d3ob01507f

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Total Synthesis of (+)-Coriamyrtin via a Desymmetrizing Strategy Involving a 1,3-Cyclopentanedione Moiety2023

    • Author(s)
      Ikeuchi Kazutada、Haraguchi Shota、Fujii Ryo、Yamada Hidetoshi、Suzuki Takahiro、Tanino Keiji
    • Journal Title

      Organic Letters

      Volume: - Issue: 16 Pages: 2751-2755

    • DOI

      10.1021/acs.orglett.3c00249

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 2-Alkyl-2-(2-furanyl)-1,3-cyclopentanediones2023

    • Author(s)
      Ikeuchi Kazutada、Tanino Keiji、Ozoe Yusuke、Kato Ranmaru、Suzuki Takahiro
    • Journal Title

      Synthesis

      Volume: - Issue: 10 Pages: 1525-1532

    • DOI

      10.1055/a-2004-1333

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solanoeclepin B, a hatching factor for potato cyst nematode2023

    • Author(s)
      Shimizu Kosuke、Akiyama Ryota、Okamura Yuya、Ogawa Chihiro、Masuda Yuki、Sakata Itaru、Watanabe Bunta、Sugimoto Yukihiro、Kushida Atsuhiko、Tanino Keiji、Mizutani Masaharu
    • Journal Title

      Science Advances

      Volume: 9 Issue: 11

    • DOI

      10.1126/sciadv.adf4166

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Diastereoselective Synthesis of trans-anti-Hydrophenanthrenes via Ti-mediated Radical Cyclization and Total Synthesis of Kamebanin2023

    • Author(s)
      Suzuki Takahiro、Ikeda Wataru、Kanno Ayaka、Ikeuchi Kazutada、Tanino Keiji
    • Journal Title

      Chemistry A European Journal

      Volume: 29 Issue: 17

    • DOI

      10.1002/chem.202203511

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Model Synthetic Study of Tutin, a Picrotoxane-Type Sesquiterpene: Stereoselective Construction of a <i>cis</i>-Fused 5,6-Ring Skeleton2022

    • Author(s)
      Ikeuchi Kazutada、Haraguchi Shota、Yamada Hidetoshi、Tanino Keiji
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 70 Issue: 6 Pages: 435-442

    • DOI

      10.1248/cpb.c22-00083

    • ISSN
      0009-2363, 1347-5223
    • Year and Date
      2022-06-01
    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis and Structural Revision of the 6,11-Epoxyisodaucane Natural Sesquiterpene Using an Anionic 8π Electrocyclic Reaction2022

    • Author(s)
      Kato Ranmaru、Saito Hiroki、Ikeuchi Kazutada、Suzuki Takahiro、Tanino Keiji
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 43 Pages: 7939-7943

    • DOI

      10.1021/acs.orglett.2c03068

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Lipid Droplet Formation Is Regulated by Ser/Thr Phosphatase PPM1D via Dephosphorylation of Perilipin 12022

    • Author(s)
      Kamada Rui、Uno Sae、Kimura Nozomi、Yoshimura Fumihiko、Tanino Keiji、Sakaguchi Kazuyasu
    • Journal Title

      International Journal of Molecular Sciences

      Volume: 23 Issue: 19 Pages: 12046-12046

    • DOI

      10.3390/ijms231912046

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of 2-Isocyanoallopupukeanane: Construction of Caged Skeleton by Intramolecular Alkylation of Bromonitriles2022

    • Author(s)
      Kato Kosuke、Ikeuchi Kazutada、Suzuki Takahiro、Tanino Keiji
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 35 Pages: 6407-6411

    • DOI

      10.1021/acs.orglett.2c02434

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Two-Step Method for Constructing a Quaternary Carbon Atom with a Geminal Divinyl Group from a Ketone2022

    • Author(s)
      Ogura Ryota、Satoh Kazuto、Kiuchi Wataru、Kato Kosuke、Ikeuchi Kazutada、Suzuki Takahiro、Tanino Keiji
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 28 Pages: 5040-5044

    • DOI

      10.1021/acs.orglett.2c01799

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic Studies toward Tubiferal A: Asymmetric Synthesis of a Model ABC-Ring Compound2021

    • Author(s)
      Tanino Keiji、Yukutake Yuki、Hiramatsu Takahiro、Itoh Ryusei、Ikeuchi Kazutada、Suzuki Takahiro
    • Journal Title

      Synlett

      Volume: 33 Issue: 03 Pages: 296-300

    • DOI

      10.1055/a-1697-7477

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic Studies of Daphniphyllum Alkaloids: A New Method for the Construction of [7-5-5] All-Carbon Tricyclic Skeleton2021

    • Author(s)
      Tanino Keiji、Kishi Jun-ichiro、Ikeuchi Kazutada、Suzuki Takahiro
    • Journal Title

      Synlett

      Volume: 33 Issue: 02 Pages: 196-200

    • DOI

      10.1055/a-1682-9415

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] PPM1D Is a Therapeutic Target in Childhood Neural Tumors2021

    • Author(s)
      Jelena Milosevic, Diana Treis, Susanne Fransson, Gabriel Gallo-Oller, Baldur Sveinbjornsson B, Nina Eissler, Keiji Tanino, Kazuyasu Sakaguchi, Tommy Martinsson, Malin Wickstrom, Per Kogner, John Inge Johnsen
    • Journal Title

      Cancers

      Volume: 13 Issue: 23 Pages: 6042-6062

    • DOI

      10.3390/cancers13236042

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] 8π Electrocyclic Reaction of Phosphonate Derivatives: Access to Seven-Membered Cross-Conjugated Cyclic Trienes2021

    • Author(s)
      Saito Hiroki、Kato Ranmaru、Ikeuchi Kazutada、Suzuki Takahiro、Tanino Keiji
    • Journal Title

      Organic Letters

      Volume: 23 Issue: 24 Pages: 9606-9610

    • DOI

      10.1021/acs.orglett.1c03815

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a Bicyclo[2.2.1]heptane Skeleton with Two Oxy-Functionalized Bridgehead Carbons via the Diels?Alder Reaction2021

    • Author(s)
      Ikeuchi Kazutada、Sasage Tomonari、Yamada Gen、Suzuki Takahiro、Tanino Keiji
    • Journal Title

      Organic Letters

      Volume: 23 Issue: 23 Pages: 9123-9127

    • DOI

      10.1021/acs.orglett.1c03451

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Seven-Membered Cross-Conjugated Cyclic Trienes by 8π Electrocyclic Reaction2021

    • Author(s)
      Kato Ranmaru、Saito Hiroki、Uda Shoko、Domon Daisuke、Ikeuchi Kazutada、Suzuki Takahiro、Tanino Keiji
    • Journal Title

      Organic Letters

      Volume: 23 Issue: 22 Pages: 8878-8882

    • DOI

      10.1021/acs.orglett.1c03383

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Biomimetic Total Syntheses of (+)-Chloropupukeananin, (?)-Chloropupukeanolide D, and Chloropestolides2021

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

      The Journal of Organic Chemistry

      Volume: 86 Issue: 21 Pages: 15597-15605

    • DOI

      10.1021/acs.joc.1c02108

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Illisimonin a Skeleton by Intramolecular Diels?Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes2021

    • Author(s)
      Suzuki Takahiro、Nagahama Riko、Fariz Muhammad Aiman、Yukutake Yuki、Ikeuchi Kazutada、Tanino Keiji
    • Journal Title

      Organics

      Volume: 2 Issue: 3 Pages: 306-312

    • DOI

      10.3390/org2030016

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Presentation] アニオン性8π系電子環状反応による7員環β-ケトエステル誘導体の合成2024

    • Author(s)
      加藤 蘭丸、斎藤 優輝、谷野 圭持
    • Organizer
      日本化学会第104春季年会
    • Related Report
      2023 Annual Research Report
  • [Presentation] Cristaxenicin A の合成研究2024

    • Author(s)
      城内 航、角田 祐子、加藤 港介、谷野 圭持
    • Organizer
      日本化学会第104春季年会
    • Related Report
      2023 Annual Research Report
  • [Presentation] 新しいカゴ型骨格構築法に基づく天然物合成2023

    • Author(s)
      谷野 圭持
    • Organizer
      第67回香料・テルペンおよび精油化学に関する討論会
    • Related Report
      2023 Annual Research Report
    • Invited
  • [Presentation] 橋頭位水酸基を有する三環性ノルボルネン誘導体の骨格転位2023

    • Author(s)
      吉谷 明浩、捧 智成、加藤 蘭丸、池内 和忠、谷野 圭持
    • Organizer
      第67回香料・テルペンおよび精油化学に関する討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] 連続的ラジカル環化反応を利用したクロバン骨格の合成研究2023

    • Author(s)
      山下 公太朗、池田 航、鈴木 孝洋、谷野 圭持
    • Organizer
      第67回香料・テルペンおよび精油化学に関する討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] 1,4-ビスシロキシ-1,3-シクロペンタジエンを利用した7-ノルボルノナン骨格構築法の開発2023

    • Author(s)
      廣川歓人、捧 智成、池内和忠、谷野圭持
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] ノルボルネン骨格含有三環性化合物の骨格転位によるトリシクロ[4.2.1.03,7]ノナン誘導体の合成2023

    • Author(s)
      吉谷明浩、捧 智成、加藤蘭丸、池内和忠、谷野圭持
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] ビニルシクロプロパン転位による7員環ニトリル誘導体の合成2022

    • Author(s)
      竹内貴志、谷野圭持
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 分子内に3つのプロペラン構造を含む新規5環性カゴ状炭素骨格の合成2022

    • Author(s)
      海岸秀次、今井隆史、鈴木孝洋、谷野圭持
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Synthetic Studies on Illisimonin A2022

    • Author(s)
      Muhammad Aiman bin Mohd Fariz、鈴木孝洋、長濱梨香、行武悠樹、谷野圭持
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 2位にアルキル基とヘテロアリール基を有する1,3-シクロペンタンジオン誘導体の合成2022

    • Author(s)
      尾添祐介、加藤蘭丸、池内和忠、谷野圭持
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report

URL: 

Published: 2021-04-28   Modified: 2025-01-30  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi