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2013 Fiscal Year Final Research Report

Synthetic Studies on Bioactive Natural Products utilizing Integrated

Planned Research

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Project AreaOrganic Synthesis based on Integration of Chemical Reactions. New Methodologies and New Materials
Project/Area Number 21106009
Research Category

Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionWaseda University

Principal Investigator

NAKADA Masahisa  早稲田大学, 理工学術院, 教授 (50198131)

Co-Investigator(Kenkyū-buntansha) HAYASHI Nobuyuki  早稲田大学, 理工学術院, 助手 (90514208)
NIWA Takashi  早稲田大学, 理工学術院, 助教 (30584396)
FUJII Tomohiro  早稲田大学, 理工学術院, 助手 (00707911)
Project Period (FY) 2009-07-23 – 2014-03-31
Keywords反応集積化 / 不斉触媒反応 / 連続反応 / 不斉全合成 / 生物活性物質
Research Abstract

We have studied the total synthesis of bioactive natural products via integrated reactions developed by focusing our attention on reactive intermediates. (1)Anion: Total syntheses of (-)-scabronines G, A, D, and (-)-episcabronine A have been achieved. Highly stereoselective Michael reaction cascades have been developed. (2)Cation: A formal enantioselective total synthesis of (-)-taxol and a first total synthesis of (+)-ophiobolin A have been achieved. (3)Transition metal: Total synthesis of hyperforin, formal enantioselective total syntheses of nemorosone, garsubellin A, and clusianone have been achieved. A first non-heme Fe(III) complex that catalyzes highly enantioselective asymmetric epoxidation has been synthesized. A first enantioselective total synthesis of (+)-colletoic acid, formal total syntheses of (-)-platencin and (-)-platensimycin, integrated syntheses of a-alkylidene b-keto imide, highly enantioselective [4+2]cycloaddition and Hosomi-Sakurai reaction have been achieved.

  • Research Products

    (26 results)

All 2014 2013 2012 2011 2010 2009 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (17 results) (of which Invited: 17 results) Book (3 results) Remarks (1 results)

  • [Journal Article] Total Syntheses of (-)-Scabronines G and A, and (-)-Episcabronine2013

    • Author(s)
      A, Kobayakawa, Y.; Nakada, M. Angew
    • Journal Title

      Chem., Int. Ed (Synfacts)

      Volume: 52 Pages: 7569-7573

    • DOI

      10.1002/anie.201303224

    • Peer Reviewed
  • [Journal Article] Enantioselective Total Synthesis of (+)-Colletoic Acid via Catalytic Asymmetric Intramolecular Cyclopropanation of an α-Diazo-β-Keto Diphenylphosphine Oxide2013

    • Author(s)
      Sawada, T.; Nakada, M
    • Journal Title

      Org. Lett

      Volume: 15 Pages: 1004–1007

    • DOI

      10.1021/ol303459x

    • Peer Reviewed
  • [Journal Article] A Non-Heme Iron (III) Complex with Porphyrin-Like Properties that Catalyzes Asymmetric Epoxidation2012

    • Author(s)
      Niwa, T.; Nakada, M
    • Journal Title

      J. Am. Chem. Soc (Synfacts)

      Volume: 134 Pages: 13538-13541

    • DOI

      10.1021/ja304219s

    • Peer Reviewed
  • [Journal Article] Stereoselective Total Synthesis of Nemorosone2012

    • Author(s)
      Uwamori, M.; Saito, A.; Nakada, M
    • Journal Title

      J. Org. Chem

      Volume: 77 Pages: 5098-5107

    • DOI

      10.1021/jo300646j

    • Peer Reviewed
  • [Journal Article] Convergent Total Synthesis of (+)-Ophiobolin A2011

    • Author(s)
      Tsuna, K.; Noguchi, N.; Nakada, M. Angew
    • Journal Title

      Chem., Int. Ed

      Volume: 50 Pages: 9452-9455

    • DOI

      10.1002/anie.201104447

    • Peer Reviewed
  • [Presentation] Highly Efficient Total Synthesis and Biological Evaluation of (-)-Scabronines2014

    • Author(s)
      Nakada,M
    • Organizer
      International Symposium on Integration of Chemistry and Bioscience
    • Place of Presentation
      Tokyo
    • Year and Date
      2014-01-16
    • Invited
  • [Presentation] 連続反応を経由する生物活性天然物の不斉全合成2013

    • Author(s)
      中田雅久
    • Organizer
      第57回日本薬学会関東支部大会化学系シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2013-10-26
    • Invited
  • [Presentation] Total Synthesis of Bioactive Natural Products via Olefin Metathesis in Our Laboratory2013

    • Author(s)
      Nakada,M
    • Organizer
      The 20th International Symposium on Olefin Metathesis and Related Chemistry (ISOM20)
    • Place of Presentation
      Nara
    • Year and Date
      2013-07-16
    • Invited
  • [Presentation] 連続反応を鍵工程とする生物活性多環式天然物の全合成2013

    • Author(s)
      中田雅久
    • Organizer
      名古屋大学大学院工学研究科講演会
    • Place of Presentation
      名古屋
    • Year and Date
      2013-06-27
    • Invited
  • [Presentation] Development of Catalytic Asymmetric Intramolecular Cyclopropanation and Asymmetric Total Synthesis of (+)-Colletoic Acid2013

    • Author(s)
      Nakada, M
    • Organizer
      The 4^<th> Symposium on Chiral Science & Technology
    • Place of Presentation
      Tokyo
    • Year and Date
      2013-03-01
    • Invited
  • [Presentation] 新合成手法の開発と生物活性多環式天然物の不斉全合成2012

    • Author(s)
      中田雅久
    • Organizer
      東京理科大学大学院薬学研究科講演会
    • Place of Presentation
      東京理科大学大学院薬学研究科東京理科大学野田キャンパス、千葉
    • Year and Date
      2012-10-02
    • Invited
  • [Presentation] 生物活性多環式含歪天然物の不斉全合成研究2012

    • Author(s)
      中田雅久
    • Organizer
      第29回有機合成化学セミナー(2012)
    • Place of Presentation
      静岡県コンベンションアーツセンター、静岡
    • Year and Date
      2012-09-06
    • Invited
  • [Presentation] 生物活性天然物の不斉全合成2012

    • Author(s)
      中田雅久
    • Organizer
      有機合成化学協会東北支部主催・仙台地区春の講演会
    • Place of Presentation
      東北大学薬学部、仙台
    • Year and Date
      2012-06-30
    • Invited
  • [Presentation] Total Synthesis of Natural Products via Catalytic Asymmetric Intramolecular Cyclopropanation (CAIMCP)2012

    • Author(s)
      Nakada, M
    • Organizer
      The 3rd International Symposium on Organic Synthesis and Drug Development (ISOSDD)
    • Place of Presentation
      Changzhou, China
    • Year and Date
      2012-05-22
    • Invited
  • [Presentation] Total Synthesis of Natural Products via Catalytic Asymmetric Intramolecular Cyclopropanation (CAIMCP)2012

    • Author(s)
      Nakada, M
    • Organizer
      The 3rd Annual World Congress of Catalytic Asymmetric Synthesis-2012 (WCCAS-2012)
    • Place of Presentation
      Beijing, China
    • Year and Date
      2012-05-14
    • Invited
  • [Presentation] 触媒的不斉分子内シクロプロパン化の開発と天然物合成への活用2012

    • Author(s)
      中田雅久
    • Organizer
      第3回キラルサイエンス&テクノロジーシンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2012-02-14
    • Invited
  • [Presentation] Synthetic Studies on Nemorosone2011

    • Author(s)
      Nakada, M
    • Organizer
      14th Asian Chemical Congress (14 ACC) Contemporary Chemistry for Sustainability and Economic Sufficiency
    • Place of Presentation
      Bangkok
    • Year and Date
      20110905-08
    • Invited
  • [Presentation] タキソールの効率的不斉全合成への挑戦2011

    • Author(s)
      中田雅久
    • Organizer
      第23回 万有札幌シンポジウム有機化学の深化と多様化
    • Place of Presentation
      札幌
    • Year and Date
      2011-07-02
    • Invited
  • [Presentation] タキソールの収束的不斉全合成への挑戦2010

    • Author(s)
      中田雅久
    • Organizer
      第45回天然物談話会
    • Place of Presentation
      愛知県蒲郡市
    • Year and Date
      20100706-08
    • Invited
  • [Presentation] 連続反応を鍵工程とする生物活性多環式天然物の不斉全合成研究2010

    • Author(s)
      中田雅久
    • Organizer
      日本化学会第90 春季年会
    • Place of Presentation
      大阪
    • Year and Date
      20100326-29
    • Invited
  • [Presentation] 新合成ルートによるタキソールの収束的不斉全合成への挑戦2010

    • Author(s)
      中田雅久
    • Organizer
      理研シンポジウム第5回「有機合成化学のフロンティア」
    • Place of Presentation
      埼玉県和光市
    • Year and Date
      2010-07-09
    • Invited
  • [Presentation] 有用な生物活性多環式天然物の精密不斉全合成に関する研究2009

    • Author(s)
      中田雅久
    • Organizer
      第96回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      20090610-11
    • Invited
  • [Book] トップドラッグから学ぶ創薬化学2012

    • Author(s)
      中田雅久
    • Total Pages
      171, 172, 176, 177
    • Publisher
      東京化学同人
  • [Book] 天然物合成で活躍した反応 実験のコツとポイント2011

    • Author(s)
      中田雅久、高野真史、宇津木雅之、渡邉秀昭
    • Total Pages
      36, 64, 146, 150
    • Publisher
      化学同人
  • [Book] 天然物の全合成2009

    • Author(s)
      中田雅久
    • Total Pages
      63, 74
    • Publisher
      化学同人
  • [Remarks]

    • URL

      http://www.chem.waseda.ac.jp/nakada/

URL: 

Published: 2015-06-25  

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