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Synthetic study of chiral compounds by taking advantage of an umpolung approach

Research Project

Project/Area Number 17K08216
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

Miyata Okiko  大阪市立大学, 大学院理学研究科, 客員教授 (90102110)

Co-Investigator(Kenkyū-buntansha) 品田 哲郎  大阪市立大学, 大学院理学研究科, 教授 (30271513)
武田 紀彦  神戸薬科大学, 薬学部, 講師 (30449871)
Project Period (FY) 2017-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2020: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2019: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Keywords炭素-炭素結合形成反応 / カルボニル化合物 / 極性転換 / ヘテロ原子間結合 / 結合開裂 / ヘテロ原子 / ヘテロ原子結合 / シグマトロピー転位 / 極性転換反応 / 不斉補助基 / ジアステレオ選択性 / 有機アルミニウム試薬 / エナミン / 光学活性化合物
Outline of Final Research Achievements

Development of new synthetic reactions triggered by nitrogen-oxygen bond cleavage is attempted. We found several new transformations represented by (i) the nucleophilic γ-phenylation and γ-alkylation of α,β-unsaturated amides, and (ii) α-phenylation of ketones with triphenylaluminium in the presence of (+)-benzopyranoisoxazolidine. These new methods would be a useful synthetic tool for the preparation of optically active drug candidates and biologically active molecules.

Academic Significance and Societal Importance of the Research Achievements

研究内容は査読付き国際学術雑誌に掲載されており、学術的な評価を受けている。医薬品開発研究において、光学活性体を作り分ける方法論の開発は重要な研究課題の一つである。本研究成果は健康社会の基盤となる医薬品開発に貢献する成果として、社会的意義を有している。

Report

(6 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • 2019 Research-status Report
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (32 results)

All 2021 2020 2019 2018 2017 Other

All Journal Article (12 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 10 results,  Open Access: 2 results) Presentation (16 results) (of which Int'l Joint Research: 3 results,  Invited: 1 results) Remarks (4 results)

  • [Journal Article] A Story of a Female Student Fascinated by Chemical Research2021

    • Author(s)
      Miyata Okiko
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 79 Issue: 7 Pages: 700-703

    • DOI

      10.5059/yukigoseikyokaishi.79.700

    • NAID

      130008062768

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2021-07-01
    • Related Report
      2021 Annual Research Report
  • [Journal Article] Chondroitin Sulfate N -acetylgalactosaminyltransferase-2 Impacts Foam Cell Formation and Atherosclerosis by Altering Macrophage Glycosaminoglycan Chain2021

    • Author(s)
      Adhikara Imam Manggalya、Yagi Keiko、Mayasari Dyah Samti、Suzuki Yoko、Ikeda Koji、Ryanto Gusty Rizky Teguh、Sasaki Naoto、Rikitake Yoshiyuki、Nadanaka Satomi、Kitagawa Hiroshi、Miyata Okiko、Igarashi Michihiro、Hirata Ken-ichi、Emoto Noriaki
    • Journal Title

      Arteriosclerosis, Thrombosis, and Vascular Biology

      Volume: 41 Issue: 3 Pages: 1076-1091

    • DOI

      10.1161/atvbaha.120.315789

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Selective oxidation of alcohol-d1 to aldehyde-d1 using MnO22021

    • Author(s)
      Okamura Hironori、Yasuno Yoko、Nakayama Atsushi、Kumadaki Katsushi、Kitsuwa Kohei、Ozawa Keita、Tamura Yusaku、Yamamoto Yuki、Shinada Tetsuro
    • Journal Title

      RSC Advances

      Volume: 11 Issue: 46 Pages: 28530-28534

    • DOI

      10.1039/d1ra05405h

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Sequential nucleophilic addition/1,2-rearrangement of N-iminolactam: A ring-contractive strategy for the synthesis of 2-acyl pyrrolidines2021

    • Author(s)
      Takeda Norihiko、Kobori Yukiko、Yasui Motohiro、Matsumoto Yuki、Orihara Kotomi、Kido Yusaku、Ueda Masafumi
    • Journal Title

      Tetrahedron Letters

      Volume: 73 Pages: 153098-153098

    • DOI

      10.1016/j.tetlet.2021.153098

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of (2S,6R)‐Diamino‐(5R,7)‐dihydroxy‐heptanoic Acid (DADH): An Unusual Amino Acid from Streptomyces sp. SANK 604042021

    • Author(s)
      Okamura Hironori、Yasuno Yoko、Nakayama Atsushi、Takikawa Hirosato、Shinada Tetsuro
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2021 Issue: 9 Pages: 1396-1401

    • DOI

      10.1002/ejoc.202001646

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] γ-C (sp3)-H bond functionalisation of α,β-unsaturated amides through an umpolung strategy2020

    • Author(s)
      Futaki Erika、Takeda Norihiko、Yasui Motohiro、Shinada Tetsuro、Miyata Okiko、Ueda Masafumi
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 18 Issue: 8 Pages: 1563-1566

    • DOI

      10.1039/d0ob00125b

    • Related Report
      2020 Research-status Report 2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] 第5回 有機分子や学生達と過ごした日々を振り返って2020

    • Author(s)
      宮田 興子
    • Journal Title

      Farumashia

      Volume: 56 Issue: 10 Pages: 946-947

    • DOI

      10.14894/faruawpsj.56.10_946

    • NAID

      130007920812

    • ISSN
      0014-8601, 2189-7026
    • Related Report
      2020 Research-status Report
  • [Journal Article] Synthesis of Optically Active (R)- and (S)-β-Arginine from Pyroglutamic Acid2020

    • Author(s)
      Shinada Tetsuro、Yasuno Yoko、Sawai Akira、Sekihara Ai
    • Journal Title

      HETEROCYCLES

      Volume: 101 Issue: 1 Pages: 165-176

    • DOI

      10.3987/com-19-s(f)6

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Reagent-controlled regiodivergence in the [3,3]-sigmatropic rearrangement of N-(acyloxy)enamides2019

    • Author(s)
      Takeda Norihiko、Arisawa Narumi、Miyamoto Misaki、Kobori Yukiko、Shinada Tetsuro、Miyata Okiko、Ueda Masafumi
    • Journal Title

      Organic Chemistry Frontiers

      Volume: 6 Issue: 22 Pages: 3721-3724

    • DOI

      10.1039/c9qo01109a

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Chiral isoxazolidine-mediated stereoselective umpolung α-phenylation of methyl ketones2018

    • Author(s)
      Takeda Norihiko、Furuishi Mizuki、Nishijima Yuri、Futaki Erika、Ueda Masafumi、Shinada Tetsuro、Miyata Okiko
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 16 Issue: 46 Pages: 8940-8943

    • DOI

      10.1039/c8ob02480d

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Acylative Coupling of Amine and Indole Using Chloroform as a Carbonyl Group2018

    • Author(s)
      Nishida Yuika、Takeda Norihiko、Matsuno Kenji、Miyata Okiko、Ueda Masafumi
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2018 Issue: 29 Pages: 3928-3935

    • DOI

      10.1002/ejoc.201800571

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Nucleophilic Arylation of N,O-Ketene Acetals with Triaryl Aluminum Reagents: Access to α-Aryl Amides through an Umpolung Process2017

    • Author(s)
      Takeda Norihiko、Futaki Erika、Kobori Yukiko、Ueda Masafumi、Miyata Okiko
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 56 Issue: 51 Pages: 16342-16346

    • DOI

      10.1002/anie.201708665

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] 重水素化アルデヒドの簡便合成2021

    • Author(s)
      品田哲郎、熊懐克志、橘和航平、小澤圭太、田村優作、山本悠生、中山淳、岡村仁則、保野陽子
    • Organizer
      創薬懇話会2021 in 京都
    • Related Report
      2021 Annual Research Report
  • [Presentation] 有機合成化学を基盤とするテルペン系天然物の生合成および生物機能の解明2021

    • Author(s)
      品田哲郎
    • Organizer
      有機合成化学協会 2019年度企業冠賞受賞講演会(オンライン開催)
    • Related Report
      2020 Research-status Report
    • Invited
  • [Presentation] アルデヒドの簡便な重水素化法の開発と重水素化鎖状テルペン合成への応用2021

    • Author(s)
      品田哲郎、保野陽子、岡村仁則、中山淳、熊懐克志、橘和航平、小澤圭太、田村優作、山本悠生
    • Organizer
      日本化学会 第101回春季年会(2021)
    • Related Report
      2020 Research-status Report
  • [Presentation] (2S,6R)-ジアミノ-(5R,7)-ジヒドロキシヘプタン酸(DADH)及びその誘導体の立体選択的合成2021

    • Author(s)
      岡村 仁則、保野 陽子、滝川 浩郷、品田 哲郎
    • Organizer
      日本農芸化学会 2021年度大会
    • Related Report
      2020 Research-status Report
  • [Presentation] N-アシルカルバゾールを用いた選択的アミド化反応の開発2020

    • Author(s)
      姜法雄 、保野陽子 、岡村仁則 、酒井明日実 、佐藤哲也 、久世雅樹 、品田哲郎
    • Organizer
      第62回天然有機化合物討論会
    • Related Report
      2020 Research-status Report
  • [Presentation] Synthetic Study of Phomopsin A : Catalytic Asymmetric Synthesis of β-OH-DOPA2019

    • Author(s)
      Kohei Yasuda, Yoko Yasuno, Tetsuro Shinada
    • Organizer
      27th International Sciety of Heterocyclic Chemistry Congress
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] First Total Synthesis of Antrimycin A and D2019

    • Author(s)
      Yoko Yasuno, Akito Nishimura, Akira Sawai, Ai Sekihara, Tetsuro Shinada
    • Organizer
      27th International Sciety of Heterocyclic Chemistry Congress
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] アミドの極性転換反応:α位およびγ位への求核剤導入法の開発2019

    • Author(s)
      武田紀彦、二木恵里佳、宮田興子、上田昌史
    • Organizer
      第17回次世代を担う有機化学シンポジウム
    • Related Report
      2019 Research-status Report
  • [Presentation] N-アルコキシアミドを用いた新分子変換法2019

    • Author(s)
      武田紀彦
    • Organizer
      第5回関西薬学シンポジウム:化学系の若い力
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] 極性転換反応を利用したγ‐置換アミド類合成法の開発2018

    • Author(s)
      武田紀彦、二木恵里佳、宮田興子、上田昌史
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 連続環化反応を利用した新規ヘテロ環構築法の開発研究2018

    • Author(s)
      西川翔悟、武田紀彦、二木恵里佳、上田昌史
    • Organizer
      第68回日本薬学会近畿支部総会・大会
    • Related Report
      2018 Research-status Report
  • [Presentation] 極性転換反応を利用した簡便なα-置換アミド類合成法の開発2017

    • Author(s)
      武田紀彦、小堀友規子、二木恵里佳、上田昌史、宮田興子
    • Organizer
      日本薬学会第137年会
    • Related Report
      2017 Research-status Report
  • [Presentation] Nucleophilic arylation of N,O-ketene acetals with triarylaluminums for the preparation of alfa-arylamides2017

    • Author(s)
      Erika Futaki, Norihiko Takeda, Yukiko Kobori, Okiko Miyata, Masafumi Ueda
    • Organizer
      18th Tetrahedron Symposium Asia Edition
    • Related Report
      2017 Research-status Report
  • [Presentation] メチルケトン類の立体選択的α-フェニル化反応の開発2017

    • Author(s)
      武田紀彦、古石瑞希、松野研司、宮田興子、上田昌史
    • Organizer
      第37回有機合成若手セミナー「明日の有機合成を担う人のために」
    • Related Report
      2017 Research-status Report
  • [Presentation] N,O-ケテンアセタールの求核的アリール化反応の開発2017

    • Author(s)
      武田紀彦、二木恵里佳、小堀友規子、宮田興子、上田昌史
    • Organizer
      第34回有機合成化学セミナー
    • Related Report
      2017 Research-status Report
  • [Presentation] ケトン類のα-アルコキシ化反応の開発2017

    • Author(s)
      川上智広、長尾拓磨、武田紀彦、宮田興子、上田昌史
    • Organizer
      第67回日本薬学会近畿支部総会・大会
    • Related Report
      2017 Research-status Report
  • [Remarks] 大阪市立大学大学院理学研究科物質分子系専攻分子変換学研究室

    • URL

      http://www.sci.osaka-cu.ac.jp/chem/henkan/

    • Related Report
      2021 Annual Research Report 2020 Research-status Report 2018 Research-status Report
  • [Remarks] 大阪市立大学大学院理学研究科物質分子系専攻分子変換学研究室

    • URL

      http://www.sci.osaka-cu.ac.jp/chem/henkan/index.html

    • Related Report
      2019 Research-status Report
  • [Remarks] 神戸薬科大学薬品化学研究室

    • URL

      https://www.kobepharma-u.ac.jp/medchem/publications/

    • Related Report
      2019 Research-status Report 2018 Research-status Report
  • [Remarks] 神戸薬科大学薬品化学研究室

    • URL

      http://www.kobepharma-u.ac.jp/medchem/

    • Related Report
      2017 Research-status Report

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Published: 2017-04-28   Modified: 2023-01-30  

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