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Development of the construction of multi contiguous chiral carbons by using recyclable chiral amine.

Research Project

Project/Area Number 22590024
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionKyoto Pharmaceutical University

Principal Investigator

OZEKI Minoru  京都薬科大学, 薬学部, 助教 (40465597)

Co-Investigator(Kenkyū-buntansha) YAMASHITA Masayuki  京都薬科大学, 薬学部, 教授 (20239982)
HOSOI Shinzo  京都薬科大学, 薬学部, 准教授 (60209236)
Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2012: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2011: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords不斉合成 / キラルアミン / Michael 付加 / tandem 反応 / 多連続不斉炭素 / tandem反応 / グリーンケミストリー / Michael付加反応 / α-ヒドロキシ-β-アミノ酸 / 不斉プロトン化 / tandem Michael-aldol反応 / double Michael付加反応 / tandem double Michael-aldol反応
Research Abstract

We developed the novel tandem reaction to enable the construction of the multi contiguous chiral centers taking advantage of asymmetric Michael addition of chiral amine. As a result, 2 to 5 contiguous chiral centers were finely constructed in one pot utilizing five types of Michael addition, i.e., tandem Michael-alkylation, tandem Michael-oxidation, tandem Micheal-aldol, double Michael addition and double Michael-aldol reaction, which were triggered by a nucleophilic attack of chiral amine.

Report

(4 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (43 results)

All 2013 2012 2011 2010 Other

All Journal Article (16 results) (of which Peer Reviewed: 16 results) Presentation (27 results)

  • [Journal Article] First asymmetric total synthesis of (+)-taiwaniaquinol D and (?)-taiwaniaquinone D by using intramolecular Heck reaction2013

    • Author(s)
      Minoru Ozeki, Megumi Satake, Toshinori Toizume, Shintaro Fukutome, Kenji Arimitsu, Shinzo Hosoi, Tetsuya Kajimoto, Hiroki Iwasaki, Naoto Kojima, Manabu Node, Masayuki Yamashita
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 19 Pages: 3841-3846

    • DOI

      10.1016/j.tet.2013.03.051

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Novel skeleton transformation reaction ofα-pyrone derivatives to spirobicyclo[3.1.0]hexane derivatives using dimethylsulfoxonium methylide2012

    • Author(s)
      Takuya Miura, Navnath Dnyanoba Yadav, Hiroki Iwasaki, Minoru Ozeki, Naoto Kojima, Masayuki Yamashita
    • Journal Title

      Organic Letters

      Volume: 14 Issue: 23 Pages: 6048-6051

    • DOI

      10.1021/ol302942m

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Novel approach to determining the absolute configurations at C3-positions of various types of sterols on an induced circular dichroism.2012

    • Author(s)
      Toshio Fujiwara, Yuka Taniguchi,Yukiteru Katsumoto, Takeyuki Tanaka, Minoru Ozeki, Hiroki Iwasaki, Manabu Node, Masayuki Yamashita, Shinzo Hosoi
    • Journal Title

      Steroids

      Volume: 77 Issue: 12 Pages: 1198-1204

    • DOI

      10.1016/j.steroids.2012.07.006

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Induced circular dichroism in chiral N-methyl amides possessing an achiral binaphthyl chromophore and its application to absolute configuration determination of aliphatic chiral amines2012

    • Author(s)
      Toshio Fujiwara, Yuka Taniguchi, Yukiteru Katsumoto, Takeyuki Tanaka, Manabu Node, Minoru Ozeki, Masayuki Yamashita, Shinzo Hosoi
    • Journal Title

      Tetrahedron: Asymmetry

      Volume: 23 Issue: 13 Pages: 981-991

    • DOI

      10.1016/j.tetasy.2012.06.013

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of (.+-.)-8-Deisopropyladunctin B2012

    • Author(s)
      Sayo Nomura, Kenji Arimitsu, Satoshi Yamaguchi, Yuya Kosuga, Yuko Kakimoto, Takanori Komai, Kazumasa Hasegawa, Akira Nakanishi, Tamami Miyoshi, Hiroki Iwasaki, Minoru Ozeki, Ikuo Kawasaki, Ai Kurume, Shunsaku Ohta, Masayuki Yamashita
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 60 Issue: 1 Pages: 94-103

    • DOI

      10.1248/cpb.60.94

    • NAID

      130001852353

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The First total syntheses of (+)-hostmanin A and (+)-methyllinderatin2011

    • Author(s)
      Junko Kitao, Naoko Kitamura, Nozomi Kumo, Kenji Arimitsu, Hiroki Iwasaki, Minoru Ozeki, Ai Kurume, Masayuki Yamashita
    • Journal Title

      Heterocycles

      Volume: 83 Issue: 1 Pages: 143-151

    • DOI

      10.3987/com-10-12084

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Alternative synthesis of radioiodinated trisaccharide derivatives, 2-(4-^<125>iodopheny)ethyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-D-mannopyranosyl-(1→6)-β-D-glucopyranoside, and preparation of its analogs having different lengths of alkynyl chains instead of ethyl group : acceptor substrates of N-acetylglucosaminyltransferase V for in vivo imaging2011

    • Author(s)
      Kenji Arimitsu
    • Journal Title

      Heterocycles

      Volume: 83 Issue: 12 Pages: 2779-2802

    • DOI

      10.3987/com-11-12332

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] First total synthesis of (±)-adunctin B2011

    • Author(s)
      Kenji Arimitsu, Sayo Nomura, Hiroki Iwasaki, Minoru Ozeki, Masayuki Yamashita
    • Journal Title

      Tetrahedron Lett.

      Volume: 52 Issue: 52 Pages: 7046-7048

    • DOI

      10.1016/j.tetlet.2011.10.018

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient asymmetric synthesis of abeo-abietane-type diterpenoids by using the intramolecularHeck reaction.2010

    • Author(s)
      Manabu Node, Minoru Ozeki, Loic Planas, Masashi Nakano, Hirofumi Takita, Daisuke Mori, Shinji Tamatani, Tetsuya Kajimoto
    • Journal Title

      J. Org. Chem.

      Volume: 75 Issue: 1 Pages: 190-196

    • DOI

      10.1021/jo901972b

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Glycosylation from the Non-reducing End Using a Combination of Thioglycoside and Glycosyl Sulfoxide as the Glycosyl Donor and the Acceptor2010

    • Author(s)
      Tetsuya Kajimoto, Kenji Arimitsu, Minoru Ozeki, Manabu Node
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 58 Issue: 5 Pages: 758-764

    • DOI

      10.1248/cpb.58.758

    • NAID

      130000255844

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] One-pot construction of multiple ontiguouschiral centers using Michael addtition of chiral amine.2010

    • Author(s)
      Minoru Ozeki, Shunsuke Ochi, Noboru Hayama, Shinzo Hosoi, Tetsuya Kajimoto, Manabu Node
    • Journal Title

      J. Org. Chem.

      Volume: 75 Issue: 12 Pages: 4201-4211

    • DOI

      10.1021/jo1004586

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] One-pot construction of multiple chiral centers using Michael addition of chiral amine.2010

    • Author(s)
      Minoru Ozeki
    • Journal Title

      J.Org.Chem.

      Volume: 75 Pages: 4201-4211

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient asymmetric synthesis of abeo-abietane-type diterpenoids by usine the intramolecular Heck reaction.2010

    • Author(s)
      Manabu Node
    • Journal Title

      J.Org.Chem.

      Volume: 75 Pages: 190-196

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Glycosylation from the non-reducing end using a combination of thioglycoside and glycosyl sulfoxide as the glycosyl donor and the acceptor.2010

    • Author(s)
      Tetsuya Kajimoto
    • Journal Title

      Chem.Pharm.Bull.

      Volume: 58 Pages: 758-764

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of novel asymmetric reactions and their application to the synthesis of natural products.2010

    • Author(s)
      Manabu Node
    • Journal Title

      Heterocycles

      Volume: 81 Pages: 1061-1092

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of the efficient asymmetric synthesis utilizing characteristic of chiral auxiliary.2010

    • Author(s)
      Minoru Ozeki
    • Journal Title

      J.Synth.Org.Chem.Jpn.

      Volume: 68 Pages: 854-865

    • NAID

      10026870461

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] 不斉Michael付加反応による多連続不斉炭素の構築.2013

    • Author(s)
      泉谷すみれ,中嶋大地,江川ほのか,岩崎宏樹,小島直人,小関稔,野出學,山下正行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜
    • Related Report
      2012 Final Research Report
  • [Presentation] 連続的炭素-炭素結合形成・切断によりビシクロ[3.1.0]ヘキサンを構築する新規骨格変革反応の開発2013

    • Author(s)
      三浦拓也
    • Organizer
      日本薬学会 第133年会
    • Place of Presentation
      パシフィコ横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] 不斉Michael付加反応による多連続不斉炭素の構築2013

    • Author(s)
      泉谷すみれ
    • Organizer
      日本薬学会 第133年会
    • Place of Presentation
      パシフィコ横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] メチルリンデラカルコン類の全合成研究2013

    • Author(s)
      中村麻紀子
    • Organizer
      日本薬学会 第133年会
    • Place of Presentation
      パシフィコ横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] tandem型反応による多連続不斉炭素の構築.2012

    • Author(s)
      泉谷すみれ,福留慎太郎,佐竹恵,樋爪稔典,中嶋大地,江川ほのか,岩崎宏樹,小島直人,小関稔,野出學,山下正行:キラルアミンの不斉Michael付加反応
    • Organizer
      第62回日本薬学会近畿支部総会・大会
    • Place of Presentation
      武庫川女子大学・薬学部
    • Year and Date
      2012-10-20
    • Related Report
      2012 Final Research Report
  • [Presentation] 縮還型α-ピロンからスピロビシクロ[3.1.0]ヘキサン誘導体へのタンデム骨格変換反応の開発研究2012

    • Author(s)
      三浦拓也
    • Organizer
      第38回反応と合成の進歩シンポジウム-ライフサイエンスを志向した理論、反応および合成-
    • Place of Presentation
      タワーホール船堀
    • Related Report
      2012 Annual Research Report
  • [Presentation] ヨウ化サマリウムを用いたアレンをラジカル受容体とする新規インドール骨格形成反応の開発2012

    • Author(s)
      岩﨑宏樹
    • Organizer
      第38回反応と合成の進歩シンポジウム-ライフサイエンスを志向した理論、反応および合成-
    • Place of Presentation
      タワーホール船堀
    • Related Report
      2012 Annual Research Report
  • [Presentation] キラルアミンのtandem型不斉Michael付加反応による多連続不斉炭素構築法の開発.2011

    • Author(s)
      福留慎太郎,佐竹恵,樋爪稔典,葉山登,岩崎宏樹,小関稔,野出學,山下正行
    • Organizer
      第61回日本薬学会近畿支部総会・大会
    • Place of Presentation
      神戸学院大学
    • Year and Date
      2011-10-22
    • Related Report
      2012 Final Research Report
  • [Presentation] ヨウ化サマリウムを用いた新規タンデム型スピロ環形成反応の開発-芳香環を利用した2つのスピロ中心を有する多環式化合物の合成研究-2011

    • Author(s)
      鈴木健司
    • Organizer
      第61回日本薬学会近畿支部総会・大会
    • Place of Presentation
      兵庫(神戸学院大学)
    • Year and Date
      2011-10-22
    • Related Report
      2011 Annual Research Report
  • [Presentation] (±)-Adunctin Bの全合成2011

    • Author(s)
      乾尚之
    • Organizer
      第61回日本薬学会近畿支部総会・大会
    • Place of Presentation
      兵庫(神戸学院大学)
    • Year and Date
      2011-10-22
    • Related Report
      2011 Annual Research Report
  • [Presentation] Linderachalcom類の全合成研究2011

    • Author(s)
      雲望美
    • Organizer
      第61回日本薬学会近畿支部総会・大会
    • Place of Presentation
      兵庫(神戸学院大学)
    • Year and Date
      2011-10-22
    • Related Report
      2011 Annual Research Report
  • [Presentation] キラルアミンのtandem型不斉Michael付加反応による多連続不斉炭素構築法の開発2011

    • Author(s)
      福留慎太郎
    • Organizer
      第61回日本薬学会近畿支部総会・大会
    • Place of Presentation
      兵庫(神戸学院大学)
    • Year and Date
      2011-10-22
    • Related Report
      2011 Annual Research Report
  • [Presentation] ヨウ化サマリウムを用いた新規タンデム型スピロ環形成反応の開発2011

    • Author(s)
      岩崎宏樹
    • Organizer
      第9回次世代を担う有機化学シンポジウム
    • Place of Presentation
      東京(日本薬学会長井記念ホール)
    • Related Report
      2011 Annual Research Report
  • [Presentation] ヨウ化サマリウムを用いたアレンをラジカル受容体とする新規インドール骨格形成反応の開発2011

    • Author(s)
      岩崎宏樹
    • Organizer
      第41回複素環化学討論会
    • Place of Presentation
      熊本(熊本市民会館)
    • Related Report
      2011 Annual Research Report
  • [Presentation] Adunctin Bの全合成2011

    • Author(s)
      有光健治
    • Organizer
      第37回反応と合成の進歩シンポジウム-ライフサイエンスを志向した理論、反応および合成-
    • Place of Presentation
      徳島(あわぎんホール)
    • Related Report
      2011 Annual Research Report
  • [Presentation] Synthesis and evaluation of a radiodinated trisaccharide derivatives as a synthetic substrate for a sensitive N-acetylglucosaminyltransferase V radioassay2011

    • Author(s)
      Kenji Arimitsu
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium
    • Place of Presentation
      東京(京王プラザホテル)
    • Related Report
      2011 Annual Research Report
  • [Presentation] キラルアミンのtandem型不斉Michael付加反応による多連続不斉炭素の構築.2010

    • Author(s)
      樋爪稔典,小関稔,葉山登,越智俊輔,岩崎宏樹,細井信造,梶本哲也,野出學,山下正行
    • Organizer
      第60回日本薬学会近畿支部総会・大会
    • Place of Presentation
      摂南大学・薬学部
    • Year and Date
      2010-10-30
    • Related Report
      2012 Final Research Report
  • [Presentation] キラルアミンのtandem型不斉Michael付加反応による多連続不斉炭素の構築2010

    • Author(s)
      樋爪稔典
    • Organizer
      第60回日本薬学会近畿支部総会・大会
    • Place of Presentation
      大阪(摂南大学薬学部)
    • Year and Date
      2010-10-30
    • Related Report
      2010 Annual Research Report
  • [Presentation] キラルアミンの不斉Michael付加反応を用いた多連続不斉炭素の構築2010

    • Author(s)
      小関稔
    • Organizer
      難病克服を目指した分子基盤創薬科学の開拓成果発表会
    • Place of Presentation
      京都(京都薬科大学)
    • Year and Date
      2010-03-15
    • Related Report
      2010 Annual Research Report
  • [Presentation] キラルアミンのtandem型不斉Michael付加反応による多連続不斉炭素の構築.2010

    • Author(s)
      小関稔,有光健治,越智俊輔,葉山登,岩崎宏樹,梶本哲也,細井信造,山下正行,野出學
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      ウインクあいち
    • Related Report
      2012 Final Research Report
  • [Presentation] Tandem型反応による多連続不斉炭素の立体選択的構築法の開発.2010

    • Author(s)
      葉山登,越智俊輔,小関稔,細井信三,野出學
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      岡山大学津島キャンパス他
    • Related Report
      2012 Final Research Report
  • [Presentation] Tandem型反応による多連続不斉炭素の立体選択的構築法の開発2010

    • Author(s)
      葉山登
    • Organizer
      日本薬学会 第130年会
    • Place of Presentation
      岡山(コンベンションセンター, 桃太郎アリーナ, 岡山大学津島キャンパス, 就実大学他)
    • Related Report
      2010 Annual Research Report
  • [Presentation] 誘起円二色性を基盤とするキラルアミン類の絶対配置決定について2010

    • Author(s)
      冨士原聡夫
    • Organizer
      日本薬学会 第130年会
    • Place of Presentation
      岡山(コンベンションセンター, 桃太郎アリーナ, 岡山大学津島キャンパス, 就実大学他)
    • Related Report
      2010 Annual Research Report
  • [Presentation] キラルアミンのtandem型不斉Michael付加反応による多連続不斉炭素の構築2010

    • Author(s)
      有光健治
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      愛知(ウインクあいち)
    • Related Report
      2010 Annual Research Report
  • [Presentation] 骨格変換反応によるスピロビシクロ[3.1.0]ヘキサン誘導体の新規合成法の開発

    • Author(s)
      三浦拓也
    • Organizer
      第62回日本薬学会 近畿支部総会・大会
    • Place of Presentation
      武庫川女子大学・薬学部
    • Related Report
      2012 Annual Research Report
  • [Presentation] ヨウ化サマリウムを用いたアレンをラジカル受容体とした新規インドール骨格形成反応の開発

    • Author(s)
      山根光成
    • Organizer
      第62回日本薬学会 近畿支部総会・大会
    • Place of Presentation
      武庫川女子大学・薬学部
    • Related Report
      2012 Annual Research Report
  • [Presentation] キラルアミンの不斉Michael付加反応:tandem型反応による多連続不斉炭素の構築

    • Author(s)
      泉谷すみれ
    • Organizer
      第62回日本薬学会 近畿支部総会・大会
    • Place of Presentation
      武庫川女子大学・薬学部
    • Related Report
      2012 Annual Research Report

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Published: 2010-11-30   Modified: 2019-07-29  

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