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2012 Fiscal Year Final Research Report

Efficient Synthesis of Biologically Active Natural Products Useful for Drug Discovery

Research Project

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Project/Area Number 22249001
Research Category

Grant-in-Aid for Scientific Research (A)

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

Principal Investigator

HATAKEYAMA Susumi  長崎大学, 医歯薬学総合研究科, 教授 (20143000)

Co-Investigator(Kenkyū-buntansha) ISHIHARA Jun  長崎大学, 医歯薬学総合研究科, 准教授 (80250413)
TAKAHASHI Keisuke  長崎大学, 医歯薬学総合研究科, 助教 (60380854)
Project Period (FY) 2010 – 2012
Keywords全合成 / 天然物
Research Abstract

We have studied on the total synthesis of natural products having intriguing biological activities useful for drug discovery. As a result, we have achieved the total syntheses of oxazolomycin A and kitocephalin, and the formal synthesis of welwistatin. In addition, we have developed a new methodology for the construction of heterocycles which relies on a Rh(II)-catalyzed C-H amination reaction, and have achieved the total syntheses of NW-G01, englerin A, and inthomycin A, B, C.

  • Research Products

    (23 results)

All 2012 2011 2010 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (12 results) Book (2 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results) (of which Overseas: 1 results)

  • [Journal Article] Organocatalytic Asymmetric Syntheses of Inthomycins A, B and C2012

    • Author(s)
      Madoka Yoshino, Kohei Eto, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama
    • Journal Title

      Org. Biomol. Chem.

      Volume: 10 Pages: 8164-74

    • DOI

      DOI:10.1039/c2ob26084k

    • Peer Reviewed
  • [Journal Article] Stereocontrolled Total Synthesis of (-)-Englerin A2012

    • Author(s)
      Keisuke Takahashi, Keita Komine, Yuichi Yokoi, Jun Ishihara, Susumi Hatakeyama
    • Journal Title

      J. Org. Chem

      Volume: 77 Pages: 7364-70

    • DOI

      DOI:10.1021/jo301145r

    • Peer Reviewed
  • [Journal Article] Total Synthesis of (-)-Kaitocephalin Based on a Rh-Catalyzed C-H Amination2012

    • Author(s)
      Keisuke Takahashi, Daisuke Yamaguchi, Jun ishihara, Susumi Hatakeyama
    • Journal Title

      Org. Lett

      Volume: 14 Pages: 1644-1647

    • DOI

      DOI:10.1021/ol300431n

    • Peer Reviewed
  • [Journal Article] Total Synthesis of Oxazolomycin A2011

    • Author(s)
      Kohei Eto, Madoka Yoshino, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama
    • Journal Title

      Org. Lett.

      Volume: 13 Pages: 5398-401

    • DOI

      DOI:10.1021/ol202306d

    • Peer Reviewed
  • [Journal Article] Total Synthesis of NW-G01, a Cyclic Hexapeptide Antibiotic, and 34-epi-NW-G012011

    • Author(s)
      Setsuya Shibahara, Takaaki Matsubara, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 4700-3

    • DOI

      DOI:10.1021/ol201912w

    • Peer Reviewed
  • [Journal Article] Organocatalytic Asymmetric Synthesis of Quinine and Quinidine2011

    • Author(s)
      Shaheem M. Sarkar, Yuko Taira, Ayako Nakano, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama
    • Journal Title

      Tetrahedron Lett

      Volume: 52 Pages: 923-7

    • DOI

      DOI:10.1016/j.tetlet.2010.12.066

    • Peer Reviewed
  • [Journal Article] Indium-catalyzed Conia-ene Reaction and Total Syntheses of Biologically Active Alkaloids2010

    • Author(s)
      Keisuke Takahashi, Susumi Hatakeyama
    • Journal Title

      J. Synth. Org. Chem. Jpn

      Volume: 59 Pages: 951-61

    • DOI

      DOI:10.5059/yukigoseikyokaishi.68.951

    • Peer Reviewed
  • [Presentation] α-lsocupreine, an Enantiocomplementary Catalyst of β-lsocupreidine2012

    • Author(s)
      Susumi Hatakeyama
    • Organizer
      First Japan-USA Organocatalytic Symposium
    • Place of Presentation
      Hawaii (USA)
    • Year and Date
      2012-12-17
  • [Presentation] New Entryto Substituted Pyrrolidines Based on a Rh-Catalyzed C-H Amination: Synthesis ofKaitocephalin2012

    • Author(s)
      Keisuke Takahashi, Disuke Yamaguchi, Jun Ishihara, Susumi Hatakeyama
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      Kyoto (Japan)
    • Year and Date
      2012-11-14
  • [Presentation] Welwitindolinone アルカロイドの合成研究2012

    • Author(s)
      小嶺敬太,野村祐介,Cyril Pieri,高橋圭介,石原 淳,畑山 範
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2012-11-07
  • [Presentation] ラジョラマイシンの合成研究2012

    • Author(s)
      江藤 康平,高橋圭介,石原 淳,畑山 範
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都
    • Year and Date
      2012-10-13
  • [Presentation] Claisen Rearrangement Mediated by Indium Chloride2011

    • Organizer
      22nd French-Japanese Symposium of Medicinal and Fine Chemistry
    • Place of Presentation
      Rouen (France)
    • Year and Date
      2011-12-12
  • [Presentation] Organocatalytic Asymmetric Synthesis of Inthomycin A, B and C2011

    • Author(s)
      Kohei Eto, Madoka Yoshino, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium
    • Place of Presentation
      Tokyo (Japan)
    • Year and Date
      2011-12-02
  • [Presentation] エングレリンA の全合成2011

    • Author(s)
      高橋圭介,横井裕一,小嶺敬太,石原 淳,畑山 範
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島
    • Year and Date
      2011-11-07
  • [Presentation] C-Hアミノ化を基盤とするカイトセファリンの全合成研究2011

    • Author(s)
      高橋圭介,山口大介,Lu Shenlei,石原淳,畑山 範
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪
    • Year and Date
      2011-09-29
  • [Presentation] Total Synthesis of Chloptosin2010

    • Author(s)
      Setsuya Shibahara, Takaaki Matsubara, Keishke Takahashi, Jun Ishihara, Susumi Hatakeyama
    • Organizer
      The 2010 International Chemical Congressof Pacific Basin Societies
    • Place of Presentation
      Hawaii (USA)
    • Year and Date
      2010-12-19
  • [Presentation] ピロロインドリン含有環状ヘキサペプチド類の合成研究2010

    • Author(s)
      芝原攝也,松原孝昌,高橋圭介,石原 淳,畑山 範
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2010-11-02
  • [Presentation] インソマイシン及びオキサゾロマイシン類抗生物質の合成研究2010

    • Author(s)
      江藤康平,吉野円香,高橋圭介,石原 淳,畑山 範
    • Organizer
      第52回天然有機化合物討論会
    • Place of Presentation
      静岡
    • Year and Date
      2010-10-01
  • [Presentation] New Variant of Reformasky

    • Author(s)
      Jun Ishihara, Yuki Watanabe, NorikoKoyama, Yukihiro Nishino, Keisuke Takahashi, Susumi Hatakeyama
  • [Book] Science of Synthesis: Asymmetric Organocatalysis 1 Lewis Base and Acid Catalysis2011

    • Author(s)
      Susumi Hatakeyama
    • Total Pages
      673-721
    • Publisher
      Benjamin List Ed.; Georg Thieme Verlag: New York
  • [Book] 天然物合成で活躍した反応-実験のコツとポイント(有機合成化学協会 編)2011

    • Author(s)
      畑山 範,高橋圭介
    • Total Pages
      20-1.50-1.58-9.186-7
    • Publisher
      化学同人
  • [Remarks]

    • URL

      http://www.ph.nagasaki-u.ac.jp/lab/manufac/index-j.html

  • [Patent(Industrial Property Rights)] 新規キノリン誘導体およびこれを含有する有機触媒2012

    • Inventor(s)
      畑山 範、石原 淳、高橋圭介、中本義人
    • Industrial Property Rights Holder
      長崎大学
    • Industrial Property Number
      特願2012-253343
    • Filing Date
      2012-11-19
    • Overseas

URL: 

Published: 2014-08-29  

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