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

Development of Frieden-Crafts type reactions and their applications to heterocyclic molecule syntheses

Research Project

Project/Area Number 15K07850
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionChiba University

Principal Investigator

Nemoto Tetsuhiro  千葉大学, 大学院薬学研究院, 教授 (80361450)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
KeywordsFriedel-Crafts反応 / 脱芳香化 / インドール / 天然物合成 / 銀カルベノイド / フリーデルクラフツ反応 / カスケード反応 / パラジウム / フリーデルークラフツ反応 / 遷移金属触媒 / プラチナ
Outline of Final Research Achievements

We developed the following synthetic methods in this study. (1) We developed a silver-caebenoid mediate ipso-Friedel-Crafts type intramolecular dearomatization of phenols. This process could be extended to the asymmetric reaction using chiral phosphoric acid ligands. (2) We developed a synthetic method of 3,4-fused tricyclic indole derivatives using 3,4-fused 3-alkylidene indolines as their precursors. Two types of cascade processes were developed based on palladium catalysis and platinum catalysis. (3) Using the developed methods, we succeeded in the total synthesis of (-)-aurantioclavine and fargesine. Synthetic studies of dragmacidin E were also examined using the developed palladium catalysis. In addition, we developed a synthetic method of 3,4-fused tetrahydrobenzopyranes using para-quinonemethides as key intermediates.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (34 results)

All 2018 2017 2016 2015 Other

All Int'l Joint Research (1 results) Journal Article (11 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 11 results,  Acknowledgement Compliant: 6 results) Presentation (22 results) (of which Int'l Joint Research: 3 results,  Invited: 2 results)

  • [Int'l Joint Research] University of Turku(フィンランド)

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Enantioselective formal synthesis of (-)-aurantioclavine using Pd-catalyzed cascade cyclization and organocatalytic asymmetric aziridination2018

    • Author(s)
      Shun-ichi Nakano, Yasumasa Hamada. , Tetsuhiro Nemoto,
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Issue: 8 Pages: 760-762

    • DOI

      10.1016/j.tetlet.2018.01.033

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Merging Bronsted Acid and Hydrogen-Bonding Catalysis: Metal-Free Dearomatization of Phenols via ipso-Friedel-Crafts Alkylation to Produce Functinalized Spirolactams2018

    • Author(s)
      Shingo Harada, Irene Kwok, Hiroki Nakayama, Ayaka Kanda, and Tetsuhiro Nemoto
    • Journal Title

      Adv. Synth. Catal.

      Volume: 360 Issue: 4 Pages: 801-807

    • DOI

      10.1002/adsc.201701287

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Binary Additive Effect of Benzoic Acid in ipso-Friedel-Crafts Type Dearomatization of Phenols Using Chiral Silver Phosphate2018

    • Author(s)
      Hiroki Nakayama, Shingo Harada, Ayaka Kanda, Irene Mei-Yi Kwok, and Tetsuhiro Nemoto
    • Journal Title

      Tetrahedron Lett.

      Volume: 74 Issue: 20 Pages: 2435-2439

    • DOI

      10.1016/j.tet.2018.03.060

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Acid-Promoted Cascade Cyclization to Produce 2-(4’-Alkoxyaryl)-3,4-Fused Tricyclic Dihydrobenzopyrans via a para-vinylidene quinone methide intermediate2018

    • Author(s)
      Dongil Choi, Naoki Shiga, Robert Franzen, and Tetsuhiro Nemoto
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 印刷中 Issue: 15 Pages: 1785-1788

    • DOI

      10.1002/ejoc.201800013

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Chemoselective Asymmetric Intramolecular Dearomatization of Phenols with alpha-Diazoacetamides Catalyzed by Silver Phosphate2017

    • Author(s)
      Hiroki Nakayama, Shingo Harada, Masato Kono, and Tetsuhiro Nemoto
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 139 Issue: 30 Pages: 10118-10191

    • DOI

      10.1021/jacs.7b04813

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic Study of Dragamcidin E: Construction of the Core Structure Using Pd-Catalyzed Cascade Cyclization and Rh-Catalyzed Aminoacetoxylation2017

    • Author(s)
      Naoya Inoue, Shun-ichi Nakano, Shingo Harada, Yasumasa Hamada, and Tetsuhiro Nemoto
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 5 Pages: 2787-2793

    • DOI

      10.1021/acs.joc.7b00083

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Spirocyclic and Fused Cyclic Compounds by Transition-Metal-Catalyzed Intramolecular Friedel-Crafts-Type Reactions of Phenol Derivatives2016

    • Author(s)
      Tetsuhiro Nemoto and Yasumasa Hamada
    • Journal Title

      Synkett

      Volume: 27 Issue: 16 Pages: 2301-2313

    • DOI

      10.1055/s-0035-1561470

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Platinum-Catalyzed Friedel-Crafts-Type C–H Coupling–Allylic Amination Cascade to Synthesize 3,4-Fused Tricyclic Indoles2016

    • Author(s)
      Yuta Suzuki, Yuito Tanaka, Shun-ichi Nakano, Kousuke Dodo, Natsumi Yoda, Ken-ichi Shinohara, Kazuko Kita, Atushi Kaneda, Mikiko Sodeoka, Yasumasa Hamada, and Tetsuhiro Nemoto
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 13 Pages: 4418-4421

    • DOI

      10.1002/chem.201600375

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Pd-Catalyzed Cascade Cyclization by Intramolecular Heck Insertion of an Allene–Allylic Aminaiton Sequence: Application to the Synthesis of 3,4-Fused Tricyclic Indoles2015

    • Author(s)
      Shun-ichi Nakano, Naoya Inoue, Yasumasa Hamada, and Tetsuhiro Nemoto
    • Journal Title

      Org. Lett.

      Volume: 17 Issue: 11 Pages: 2622-2625

    • DOI

      10.1021/acs.orglett.5b00973

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Spirocyclic or Fused Cyclic Compounds Using Transition Metal-Catalyzed Dearomatization of Phenols2015

    • Author(s)
      Tetsuhiro Nemoto, and Yasumasa Hamada
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 73 Issue: 10 Pages: 977-986

    • DOI

      10.5059/yukigoseikyokaishi.73.977

    • NAID

      130005109735

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Diastereoselective Synthesis of Tri-substituted Cyclopropanes Using a Pd-Catalyzed Intramoelcular Allylic Alkylation of α-Aryl Esters2015

    • Author(s)
      Tetsuhiro Nemoto, Kazuki Tsuruda, Mariko Yoshida, Masato Kono, and Yasumasa Hamada
    • Journal Title

      Synthesis

      Volume: 47 Issue: 24 Pages: 3914-3924

    • DOI

      10.1055/s-0035-1560658

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Synthesis of 3,4-Fused Tricyclic Indoles2018

    • Author(s)
      Tetsuhiro Nemoto
    • Organizer
      International Congress on Pure & Applied Chemistry (ICPAC) 2018
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] ドラグマシジンEの合成研究2018

    • Author(s)
      丸岡花香、崔東一、井上直也、仲野駿一、根本哲宏
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] para-ビニリデンキノンメチド中間体を経由する3,4位縮環2―ヒドロキシアリールジヒドロベンゾピラン類の合成法開発2018

    • Author(s)
      崔東一、滋賀直樹、Robert Franzen、根本哲宏
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 銀カルベノイドの特性を生かしたインドール類の化学選択的な不斉脱芳香化反応の開発2018

    • Author(s)
      神田彩香、中山弘貴、原田慎吾、根本哲宏
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Pd触媒によるカスケード反応を利用した(-)-Aurantioclavineの合成研究2017

    • Author(s)
      仲野駿一、濱田康正、根本哲宏
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-25
    • Related Report
      2016 Research-status Report
  • [Presentation] 銀触媒による化学およびエナンチオ選択的なフェノール類のスピロ環化反応の開発2017

    • Author(s)
      中山弘貴、原田慎吾、根本哲宏
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-25
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthetic study of dragmacidin E: Construction of the core structure usiong Pd-catalyzed cascade cyclization and Rh-catalyzed aminoacetoxylation2017

    • Author(s)
      Naoya Inoue, Shun-ichi Nakano, Shingo Harada, Yasumasa Hamada, Tetsuhiro Nemoto
    • Organizer
      The 2nd Symposium of Chiral Material Science 2017
    • Place of Presentation
      千葉
    • Year and Date
      2017-03-08
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] リン酸銀触媒を用いたジアゾアセトアミドを有するフェノール類の不斉脱芳香族化反応2017

    • Author(s)
      原田慎吾、中山弘貴、河野将人、根本哲宏
    • Organizer
      第43回反応と合成の進歩シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] リン酸銀触媒を用いたジアゾアセトアミドを有するフェノール類の不斉脱芳香族化反応2017

    • Author(s)
      中山弘貴、原田慎吾、河野将人、根本哲宏
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] para-ビニリデンキノンメチド中間体を経由する3,4位縮環2―ヒドロキシアリールジヒドロベンゾピラン類の合成法開発2017

    • Author(s)
      崔東一、滋賀直樹、根本哲宏
    • Organizer
      第61回日本薬学会関東支部大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis of 3,4-Fused Tricyclic Indoles Using Transition Metal Catalysis2017

    • Author(s)
      Tetsuhiro Nemoto
    • Organizer
      26th ISHC Conference
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 銀カルベノイドの特性を活かしたフェノール類の不斉スピロ環化反応の開発2016

    • Author(s)
      中山弘貴、原田慎吾、根本哲宏
    • Organizer
      第110回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2016-11-11
    • Related Report
      2016 Research-status Report
  • [Presentation] 白金触媒による分子内フリーデルークラフツ型アルキル化―アリル位アミノ化カスケード反応を鍵工程とするファルゲシンの合成研究2016

    • Author(s)
      田中唯人、鈴木雄太、濱田康正、根本哲宏
    • Organizer
      第42回反応と合成の進歩シンポジウム
    • Place of Presentation
      清水
    • Year and Date
      2016-11-08
    • Related Report
      2016 Research-status Report
  • [Presentation] Dragmacidin Eの合成研究2016

    • Author(s)
      井上直也、仲野駿一、濱田康正、根本哲宏
    • Organizer
      第42回反応と合成の進歩シンポジウム
    • Place of Presentation
      清水
    • Year and Date
      2016-11-07
    • Related Report
      2016 Research-status Report
  • [Presentation] Dragmacidin Eの合成研究2016

    • Author(s)
      井上直也、仲野駿一、濱田康正、根本哲宏
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-29
    • Related Report
      2015 Research-status Report
  • [Presentation] 触媒的分子内フリーデルクラフツ型アルキル化反応による新規3,4位縮環型三環性インドール骨格合成法の開発と生物活性評価2015

    • Author(s)
      鈴木雄太、田中唯人、仲野駿一、どど孝介、袖岡幹子、濱田康正、根本哲宏
    • Organizer
      第33回メディシナルケミストリーシンポジウム
    • Place of Presentation
      幕張
    • Year and Date
      2015-11-25
    • Related Report
      2015 Research-status Report
  • [Presentation] 触媒的分子内フリーデル・クラフツ型アルキル化反応による新規3,4位縮環型三環性インドール骨格合成法の開発2015

    • Author(s)
      鈴木雄太、田中唯人、濱田康正、根本哲宏
    • Organizer
      第45回複素環化学討論会
    • Place of Presentation
      早稲田大学
    • Year and Date
      2015-11-20
    • Related Report
      2015 Research-status Report
  • [Presentation] Pd触媒による分子内Heck挿入-アミノ環化カスケードによる3,4位縮環インドリンの合成法の開発2015

    • Author(s)
      仲野駿一、井上直也、濱田康正、根本哲宏
    • Organizer
      第45回複素環化学討論会
    • Place of Presentation
      早稲田大学
    • Year and Date
      2015-11-20
    • Related Report
      2015 Research-status Report
  • [Presentation] 遷移金属触媒を用いる3,4位中員環縮環インドール類の合成法開発2015

    • Author(s)
      鈴木雄太、仲野駿一、田中唯人、井上直也、濱田康正、根本哲宏
    • Organizer
      第41回反応と合成の進歩シンポジウム
    • Place of Presentation
      近畿大学
    • Year and Date
      2015-10-26
    • Related Report
      2015 Research-status Report
  • [Presentation] Dragmacidin Eの合成研究2015

    • Author(s)
      井上直也、仲野駿一、濱田康正、根本哲宏
    • Organizer
      第59回日本薬学会関東支部大会
    • Place of Presentation
      日本大学
    • Year and Date
      2015-09-12
    • Related Report
      2015 Research-status Report
  • [Presentation] Pt触媒を用いる分子内Friedel-Crafts型アルキル化反応を鍵工程としたfargesineの合成研究2015

    • Author(s)
      田中唯人、鈴木雄太、濱田康正、根本哲宏
    • Organizer
      第59回日本薬学会関東支部大会
    • Place of Presentation
      日本大学
    • Year and Date
      2015-09-12
    • Related Report
      2015 Research-status Report
  • [Presentation] 遷移金属触媒を用いる骨格構築反応の開発2015

    • Author(s)
      根本哲宏
    • Organizer
      特別講演
    • Place of Presentation
      名城大学
    • Year and Date
      2015-08-29
    • Related Report
      2015 Research-status Report
    • Invited

URL: 

Published: 2015-04-16   Modified: 2019-03-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi