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2012 Fiscal Year Final Research Report

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

Research Project

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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
Keywords不斉合成 / キラルアミン / Michael 付加 / tandem 反応 / 多連続不斉炭素
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.

  • Research Products

    (17 results)

All 2013 2012 2011 2010

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (6 results)

  • [Journal Article] First asymmetric total synthesis of (+)-taiwaniaquinol D and (-)-taiwaniaquinone D by using intramolecular Heck reaction.2013

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

      Tetrahedron

      Volume: 69 Pages: 3841-3846

    • DOI

      doi:10.1016/j.tet.2013.03.051

    • Peer Reviewed
  • [Journal Article] Novel skeleton transformation reaction of α-pyrone derivatives to spirobicyclo[3.1.0]hexane derivatives using dimethylsulfoxonium methylide.2012

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

      Org. Lett.

      Volume: 14 Pages: 6048-6051

    • DOI

      doi:10.1021/ol302942m

    • 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 Pages: 1198-1204

    • DOI

      doi:10.1016/j.steroids.2012.07.006

    • Peer Reviewed
  • [Journal Article] Inducedcircular dichroism in chiral N-methyl amides possessing an achiral binaphtyl chromophore and its application to absolute configuration determination of aliphatic chiral amines.2012

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

      Tetrahedron: Asymmetry

      Volume: 23 Pages: 891-991

    • DOI

      doi:10.1016/j.tetasy.2012.06.013

    • Peer Reviewed
  • [Journal Article] Synthesis of(±)-8-deisoprppyladunctin B. Chem.2012

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

      Pharm. Bull.

      Volume: 60 Pages: 94-103

    • DOI

      doi:10.1248/cpb.60.94

    • Peer Reviewed
  • [Journal Article] The first total syntheses of (+)-hostmanin A and (+)-methyllinderatin.2011

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

      Heterocycles

      Volume: 83 Pages: 143-151

    • DOI

      doi:10.3987/COM-10-12084

    • Peer Reviewed
  • [Journal Article] Alternative Synthesis of Radioiodinated Trisaccharide Derivatives,2-(4-125Iodophenyl)ethyl2-Acetamido-2-deoxy-SS-D-glucopyranosyl-(1→2)-α-D-mannopyranosyl-(1→6)-SS-D- glucopyranoside, and Preparation of Its Analogs Having Different Lengths of Alkyl Chains Instead of Ethyl Group: Acceptor Substrates ofN-Acetylglucosaminyltransferase V forin vivo Imaging.2011

    • Author(s)
      Kenji Arimitsu, Tetsuya Kajimoto, Hiroyuki Kimura, Masahiro Ono, MinoruOzeki, Manabu Node, Yoshiro Ohmomo, Hideo Saji, Masayuki Yamashita
    • Journal Title

      Heterocycles

      Volume: 83 Pages: 2779-2802

    • DOI

      doi:10.3987/COM-11-12332

    • Peer Reviewed
  • [Journal Article] First total synthesis of (±)-adunctin B.2011

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

      Tetrahedron Lett.

      Volume: 83 Pages: 143-151

    • DOI

      doi:10.1016/j.tetlet.2011.10.018

    • 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 Pages: 190-196

    • DOI

      doi:10.1021/jo901972b

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

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

      Chem. Pharm. Bull.

      Volume: 58 Pages: 758-764

    • DOI

      doi:10.1248/cpb.58.758

    • 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 Pages: 4201-4211

    • DOI

      doi:10.1021/jo1004586

    • 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
    • Year and Date
      20130327-30
  • [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
  • [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
  • [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
    • Year and Date
      20101101-02
  • [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
    • Year and Date
      20100328-30
  • [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

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Published: 2014-08-29  

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