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2010 Fiscal Year Final Research Report

Development of environmentally benign synthesis towards new biologically active substance

Research Project

  • PDF
Project/Area Number 20510203
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Living organism molecular science
Research InstitutionKeio University

Principal Investigator

NISHIYAMA Shigeru  Keio University, 理工学部, 教授 (20137988)

Co-Investigator(Kenkyū-buntansha) MAKI SHOJIRO  電気通信大学, 電気通信学部, 助教 (20266349)
Project Period (FY) 2008 – 2010
Keywords天然物有機化学
Research Abstract

Anodic oxidation of halogenated phenols, which was an efficient synthetic protocol of diaryl ethers shared by isodityrosine natural products, enabled optimization of cyclization reaction towards eurypamide, synthesis of diarylheptanolides, and methylthalibrine. Electrochemically generated hypervalent iodine oxidant was utilized for a synthesis of quinolinone derivatives, some of which were intermediates of tetrahydropyrroloiminoquinone alkaloids. Oxidation of aminodiaryls with the same oxidant provided carbazoles. Generation of methoxy radicals by BDD electrode in methanol solution was assessed, and reaction mechanism by this radical was discussed in neolignan synthesis.

  • Research Products

    (38 results)

All 2011 2010 2009 2008 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (29 results) Book (1 results)

  • [Journal Article] Synthesis of tetrahydropyrroloiminoquinone alkaloids based on electrochemically generated hypervalent iodine oxidative cyclization.2010

    • Author(s)
      K.Inoue, Y.Ishikawa, S.Nishiyama
    • Journal Title

      Organic Letters 12(3)

      Pages: 436-439

    • Peer Reviewed
  • [Journal Article] Electrochemical construction of the diaryl ethers : a synthetic approach to o-methylthalibrine.2010

    • Author(s)
      Y.Naito, T.Tanabe, Y.Kawabata, Y.Ishikawa, S.Nishiyama
    • Journal Title

      Tetrahedron Letters 51(36)

      Pages: 4776-4778

    • Peer Reviewed
  • [Journal Article] A synthetic approach to carbazoles using electrochemically generated hypervalent iodine oxidant.2010

    • Author(s)
      D.Kajiyama, Y.Ishikawa, S.Nishiyama
    • Journal Title

      Tetrahedron 66(52)

      Pages: 9779-9784

    • Peer Reviewed
  • [Journal Article] Synthetic studies of mangostin derivatives with an inhibitory activity on PDGF-induced human aortic smooth cells proliferation.2009

    • Author(s)
      Y.Nishihama, T.Ogamino, W.L.Shi, B.-Y.Cha, T.Yonezawa, T.Teruya, K.Nagai, K.Suenaga, J.-T.Woo, S.Nishiyama
    • Journal Title

      HETEROCYCLES 77(2)

      Pages: 759-765

    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed aromatic C-H halogenation with hydrogen halides by means of electrochemical oxidation.2009

    • Author(s)
      F.Kakiuchi, T.Kochi, H.Mutsutani, N.Kobayashi, S.Urano, M.Sato, S.Nishiyama, T.Tanabe
    • Journal Title

      Journal of the American Chemical Society 131(32)

      Pages: 11310-11311

    • Peer Reviewed
  • [Journal Article] Synthesis and antitumor activity of combretastatin D-4.2008

    • Author(s)
      K.Uno, T.Tanabe, T.Ogamino, R.Okada, M.Imoto, S.Nishiyama, K.Uno, T.Tanabe, T.Ogamino, R.Okada, M.Imoto, S.Nishiyama
    • Journal Title

      HETEROCYCLES 75(2)

      Pages: 291-296

    • Peer Reviewed
  • [Journal Article] Effects of aromatic substituents of electrochemically generated hypervalent iodine oxidant on oxidation reactions.2008

    • Author(s)
      Y.Amano, S.Nishiyama
    • Journal Title

      HETEROCYCLES 75(8)

      Pages: 1997-2003

    • Peer Reviewed
  • [Journal Article] Oxidative access to quinolinone derivatives with simultaneous rearrangement of functional groups.

    • Author(s)
      Y.Amano, K.Inoue, S.Nishiyama
    • Journal Title

      Synlett 2008(1)

      Pages: 134-136

    • Peer Reviewed
  • [Presentation] 陽極酸化法を鍵段階としたo-methylthalibrineの合成研究2011

    • Author(s)
      川端有紀,内藤雄,石川裕一,西山繁
    • Organizer
      電気化学会第76回大会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-31
  • [Presentation] 有機電気化学的手法により調製した超原子価ヨウ素試薬の化学2011

    • Author(s)
      梶山大地,井上柱輔,石川裕一,西山繁
    • Organizer
      電気化学会第76回大会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-31
  • [Presentation] BDD電極を用いた陽極酸化反応によるネオリグナンの合成2011

    • Author(s)
      角武法,斉藤毅,夏井敬介,山本崇史,石川裕一,栄長泰明,西山繁
    • Organizer
      電気化学会第76回大会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-31
  • [Presentation] 有機電極反応を活用したカルバゾール骨格含有天然物の合成研究2011

    • Author(s)
      梶山大地,井上柱輔,石川裕一,西山繁
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-29
  • [Presentation] 陽極酸化法を鍵段階としたo-methylthalibrineの合成研究2011

    • Author(s)
      川端有紀,内藤雄,石川裕一,西山繁
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-29
  • [Presentation] スピロイソキサゾリン類の合成2011

    • Author(s)
      松井香織,斉藤毅,石川裕一,西山繁
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-29
  • [Presentation] 陽極酸化反応による生物活性天然物の合成2011

    • Author(s)
      角武法,斉藤毅,夏井敬介,山本崇史,石川裕一,栄長泰明,西山繁
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-28
  • [Presentation] Electrochemical method for natural products synthesis.2010

    • Author(s)
      T.Saitoh, T.Sumi, K.Natsui, T.Yamamoto, Y.Ishikawa, Y.Einaga, S.Nishiyama
    • Organizer
      PACIFICHEM
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-18
  • [Presentation] Synthetic studies on biologically important organic molecules by means of electrochemical technology.2010

    • Author(s)
      S. Nishiyama, Y.Ishikawa
    • Organizer
      The 61st ISE Meeting
    • Place of Presentation
      Nice, France
    • Year and Date
      2010-09-30
  • [Presentation] ホタル生物発光をモデルとした発光系の創製2010

    • Author(s)
      西山繁
    • Organizer
      第19回日本バイオイメージング学会学術集会
    • Place of Presentation
      横浜
    • Year and Date
      2010-09-09
  • [Presentation] BDD電極を用いた陽極酸化反応によるリグナン及びネオリグナンの合成研究2010

    • Author(s)
      角武法,斉藤毅,夏井敬介,山本崇史,石川裕一,栄長泰明,西山繁
    • Organizer
      2010年電気化学秋季大会
    • Place of Presentation
      厚木
    • Year and Date
      2010-09-02
  • [Presentation] 有機電極反応を活用するカルバゾール骨格含有天然物の合成研究2010

    • Author(s)
      梶山大地,井上桂輔,石川裕一,西山繁
    • Organizer
      2010年電気化学秋季大会
    • Place of Presentation
      厚木
    • Year and Date
      2010-09-02
  • [Presentation] 陽極酸化法を鍵段階としたo-methylthalibrine及びジアリールエーテル骨格含有生物活性化合物の合成研究2010

    • Author(s)
      川端有紀,内藤雄,石川裕一,西山繁
    • Organizer
      新規素材探索研究会第9回セミナー
    • Place of Presentation
      横浜
    • Year and Date
      2010-06-11
  • [Presentation] 有機電極反応を活用するカルバゾール骨格含有天然物の合成研究2010

    • Author(s)
      梶山大地,井上柱輔,石川裕一,西山繁
    • Organizer
      新規素材探索研究会第9回セミナー
    • Place of Presentation
      横浜
    • Year and Date
      2010-06-11
  • [Presentation] Synthesis of epoxyquinols via anodic oxidation and evaluation of NF-kB inhibitory activity.2010

    • Author(s)
      T.Saitoh, E.Suzuki, A.Takasugi, R.Obata, Y.Ishikawa, K.Umezawa, S.Nishiyama
    • Organizer
      The 217th ECS Meeting
    • Place of Presentation
      Vancouver
    • Year and Date
      2010-04-25
  • [Presentation] Synthesis of (±)-parasitenone, a novel inhibitor of NF-KB.2009

    • Author(s)
      T.Saito, E.Suzuki, A.Takasugi, R.Obata, Y.Ishikawa, K.Umezawa, S.Nishiyama
    • Organizer
      The 11^<th> International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-11)
    • Place of Presentation
      Kyoto
    • Year and Date
      2009-11-11
  • [Presentation] Synthesis of Pyrroloiminoquinones Based on the Electrochemical Method.2009

    • Author(s)
      K.Inoue, Y.Ishikawa, S.Nishiyama
    • Organizer
      The 216th ECS Meeting
    • Place of Presentation
      Viena
    • Year and Date
      2009-10-05
  • [Presentation] Electrochemical Multistep approach toward isodityrosine : a component of biologically important cyclic peptides.2009

    • Author(s)
      K.Uno, T.Tanabe, S.Nishiyama
    • Organizer
      The 216th ECS Meeting
    • Place of Presentation
      Viena
    • Year and Date
      2009-10-05
  • [Presentation] Synthetic study of O-methylthalibrine using anodic oxidation to construct the diaryl ether moiety as a key step.2009

    • Author(s)
      Y.Naito, T.Tanabe, Y.Ishikawa, S.Nishiyama
    • Organizer
      The 216th ECS Meeting
    • Place of Presentation
      Viena
    • Year and Date
      2009-10-05
  • [Presentation] 海洋生物由来のテトラヒドロピロロイミノキノンアルカロイド類の合成2009

    • Author(s)
      井上桂輔,西山繁
    • Organizer
      電気化学76回大会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-30
  • [Presentation] 天然物を模倣したC6-C3化合物の合成研究2009

    • Author(s)
      渡辺浩太郎,石川裕一,照屋俊明,末永聖武,禹済泰,西山繁
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2009-03-28
  • [Presentation] 陽極酸化法によるジアリールエーテル骨格構築の研究2009

    • Author(s)
      内藤雄,田邊貴將,石川裕一,西山繁
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2009-03-27
  • [Presentation] エレクトロオーガニックケミストリーを活用するグリーンプロセス創製に向けて2008

    • Author(s)
      西山繁
    • Organizer
      第2回慶應義塾大学理工学部ハイテクリサーチセンターシンポジウム
    • Place of Presentation
      横浜
    • Year and Date
      2008-12-20
  • [Presentation] Synthetic studies on cyclic diarylheptanoids2008

    • Author(s)
      西山繁
    • Organizer
      The 9th International Symposium on Organic Reactions 2008-Chiayi
    • Place of Presentation
      Chiayi
    • Year and Date
      2008-11-23
  • [Presentation] 海洋天然物gymnastatin類の合成研究2008

    • Author(s)
      村山響子,田邊貴將,大西沙代,小神野孝尚,石川裕一,西山繁
    • Organizer
      第7回早慶ワークショップ
    • Place of Presentation
      横浜
    • Year and Date
      2008-09-20
  • [Presentation] フェノール酸化を活用する生物活性物質の合成に向けて2008

    • Author(s)
      西山繁
    • Organizer
      第32回エレクトロオーガニックケミストリー討論会
    • Place of Presentation
      大阪
    • Year and Date
      2008-06-26
  • [Presentation] 海洋性天然物Gymnastatin類の合成研究2008

    • Author(s)
      村山響子,田邊貴將,大西沙代,小神野孝尚,西山繁
    • Organizer
      第32回エレクトロオーガニックケミストリー討論会
    • Place of Presentation
      大阪
    • Year and Date
      2008-06-26
  • [Presentation] 有機電極反応を用いたキノリン骨格含有天然物の合成研究2008

    • Author(s)
      井上桂輔,天野良治,石川裕一,西山繁
    • Organizer
      第32回エレクトロオーガニックケミストリー討論会
    • Place of Presentation
      大阪
    • Year and Date
      2008-06-26
  • [Presentation] Electrochemical behavior of thallium ion in organic conditions and its application for organic synthesis2008

    • Author(s)
      T.Tanabe, K.Uno, Y.Ishikawa, S.Nishiyama
    • Organizer
      The 213th Meeting of the Electrochemical Society
    • Place of Presentation
      Phoenix
    • Year and Date
      2008-05-21
  • [Book] フェノール酸化を活用する生物活性物質の合成.新規素材探索-医薬品リード化合物・食品素材を求めて-(上村大輔監修 16章)2008

    • Author(s)
      西山繁
    • Total Pages
      154-164
    • Publisher
      シーエムシー出版

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Published: 2012-01-26   Modified: 2016-04-21  

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