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Synthetic study on a highly-substituted cyclic ring system including cyclobutane and a bioactive natural product causing hatching phenomenon toward potato cyst nematodes

Research Project

Project/Area Number 24580161
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionNagoya University

Principal Investigator

ADACHI Masaatsu  名古屋大学, 生命農学研究科, 助教 (80432251)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords天然物化学 / 有機化学 / 合成化学
Outline of Final Research Achievements

Synthesis of solanoeclepin A, the most active hatching agent of potato cyst nematode isolated from hydroponic potato cultures was examined not only for the chemical supply of solanoeclepin A but also for the structure-activity relationship study. As a result, we have demonstrated the power of 4-exo-trig radical cyclization for construction of the highly strained cyclobutane found in solanoeclepin A. Since the substrate is readily prepared from Hajos-Parrish ketone, samarium(II)-mediated 4-exo-trig radical cyclization could provide one of the most straightforward accessible routes to the tricyclo[5.2.1.01,6]decane skeleton of solanoeclepin A.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (43 results)

All 2015 2014 2013 2012 Other

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (32 results) (of which Invited: 2 results)

  • [Journal Article] Stereocontrolled Synthesis of ABC-tricycle of Solanoeclepin A.2015

    • Author(s)
      Adachi, M.; Torii, M.; Nishikawa, T.
    • Journal Title

      Synlett

      Volume: 26 Issue: 07 Pages: 965-969

    • DOI

      10.1055/s-0034-1380399

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of 3-Azide-4-fluoro-L-phenylalanine.2015

    • Author(s)
      Adachi, M.; Nakajima, M.; Isobe, M.
    • Journal Title

      Biosci. Biotechnol. Biochem.

      Volume: XX Issue: 5 Pages: 0-0

    • DOI

      10.1080/09168451.2014.997185

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 5- and 8-Deoxytetrodotoxin.2014

    • Author(s)
      Satake, Y.; Adachi, M.; Tokoro, S.; Yotsu-Yamashita, M.; Isobe, M.; Nishikawa, T.
    • Journal Title

      Chem. Asian. J.

      Volume: 9 Issue: 7 Pages: 1922-1932

    • DOI

      10.1002/asia.201402202

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A New Deprotection Procedure of MTM Ether.2014

    • Author(s)
      Adachi, M.; Hashimoto, H.; Sakakibara, R.; Imazu, T.; Nishikawa, T.
    • Journal Title

      Synlett

      Volume: 25 Issue: 17 Pages: 2498-2502

    • DOI

      10.1055/s-0034-1379027

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Chiriquitoxin, an Analogue of Tetrodotoxin Isolated from the Skin of a Dart Frog.2014

    • Author(s)
      Adachi, M.; Imazu, T.; Sakakibara, R.; Satake, Y.; Isobe, M.; Nishikawa, T.
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 5 Pages: 1247-1251

    • DOI

      10.1002/chem.201304110

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled Total Synthesis of Polygalolide A.2013

    • Author(s)
      Yamada, H.; Adachi, M.; Isobe, M.; Nishikawa, T.
    • Journal Title

      Chem. Asian. J.

      Volume: 8 Issue: 7 Pages: 1428-1435

    • DOI

      10.1002/asia.201300362

    • Related Report
      2013 Research-status Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] First Identification of 5,11-Dideoxytetrodotoxin in Marine Animals, and Characterization of Major Fragment Ions of Tetrodotoxin and Its Analogs by High Resolution ESI-MS/MS2013

    • Author(s)
      Mari Yotsu-Yamashita, Yuka Abe, Yuta Kudo, Raphael Ritson-Williams, Valerie J. Paul, Keiichi Konoki, Yuko Cho, Masaatsu Adachi, Takuya Imazu, Toshio Nishikawa, Minoru Isobe
    • Journal Title

      Marine Drugs

      Volume: 11 Issue: 8 Pages: 2799-2813

    • DOI

      10.3390/md11082799

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled Synthesis of the Oxathiabicylo[3.3.1]nonane Core Structure of Tagetitoxin.2013

    • Author(s)
      Yamada, H.; Adachi, M.; Isobe, M.; Nishikawa, T.
    • Journal Title

      Chem. Commun.

      Volume: 49 Issue: 95 Pages: 11221-11223

    • DOI

      10.1039/c3cc46949b

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] An Improved Synthesis of (-)-5,11-Dideoxytetrodotoxin2013

    • Author(s)
      Masaatsu Adachi, Takuya Imazu, Minoru Isobe, Toshio Nishikawa
    • Journal Title

      J. Org. Chem.

      Volume: 78 Pages: 1699-1705

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled Synthesis of an Indole Moiety of Sespendole and Stereochemical Assignment of the Side Chain2012

    • Author(s)
      Adachi, M.; Higuchi, K.; Thasana, N.; Yamada, H.; Nishikawa, T
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 1 Pages: 114-117

    • DOI

      10.1021/ol202895u

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Concise Synthesis of a Highly Strained Cyclobutane in Solanoeclepin A by Radical Cyclization2012

    • Author(s)
      Komada, T.; Adachi, M.; Nishikawa, T
    • Journal Title

      Chem. Lett.

      Volume: 41 Issue: 3 Pages: 287-289

    • DOI

      10.1246/cl.2012.287

    • NAID

      130004426518

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Total Synthesis of Chiriquitoxin, an Analogue of Tetrodotoxin Isolated from the Skin of a Dart Frog2015

    • Author(s)
      Masaatsu Adachi
    • Organizer
      日本化学会第95春季年会:日本化学会アジア国際シンポジウム
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 6-epiテトロドトキシンの合成研究2015

    • Author(s)
      橋本穂果、今津拓也、榊原 良、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2015年度大会
    • Place of Presentation
      岡山
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 電位依存性ナトリウムチャネルのサブタイプを識別するテトロドトキシン類縁体の探索2015

    • Author(s)
      千葉雪絵、塚本匡顕、長由扶子、安立昌篤、榊原良、所聖太、中崎敦夫、石川裕生、西川俊夫、山下まり、此木敬一
    • Organizer
      日本農芸化学会2015年度大会
    • Place of Presentation
      岡山
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] イリドイド類の合成研究2014

    • Author(s)
      宮澤 悠、安立昌篤、室岡孝信、宮崎雅雄、西川俊夫
    • Organizer
      日本農芸化学会中部支部第171回例会
    • Place of Presentation
      名古屋
    • Year and Date
      2014-10-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] イリドイド類の合成研究2014

    • Author(s)
      宮澤 悠、安立昌篤、室岡孝信、宮崎雅雄、西川俊夫
    • Organizer
      第49回天然物化学談話会
    • Place of Presentation
      岡山
    • Year and Date
      2014-07-02 – 2014-07-04
    • Related Report
      2014 Annual Research Report
  • [Presentation] グアニジン天然物の合成と新規イオンチャネル阻害剤の開発2014

    • Author(s)
      西川俊夫、安立昌篤、此木敬一
    • Organizer
      新学術領域研究「天然物ケミカルバイオロジー:分子標的と活性制御」第6回領域公開シンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2014-05-28 – 2014-05-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] インドールアルカロイド セスペンドールの合成研究2014

    • Author(s)
      樋口恵子、杉野公美、中崎敦夫、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2014年度大会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] MTMエーテルの新しい脱保護法の開発2014

    • Author(s)
      橋本穂果、今津拓也、榊原 良、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2014年度大会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] インドールアルカロイド セスペンドールの合成研究2013

    • Author(s)
      樋口恵子、Nopporn Thasana、山田ひと美、杉野公美、中崎敦夫、安立昌篤、西川俊夫
    • Organizer
      第48回天然化学物談話会
    • Place of Presentation
      滋賀
    • Related Report
      2013 Research-status Report
  • [Presentation] 矢毒カエル毒チリキトキシンの全合成2013

    • Author(s)
      安立昌篤、今津拓也、榊原 良、安立昌篤、佐竹佳樹、磯部 稔、西川俊夫
    • Organizer
      第55回天然有機化合物討論会
    • Place of Presentation
      京都
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of Marine Toxins Aiming at Developing Ion-Channel Inhibitors2013

    • Author(s)
      Toshio Nishikawa, Masaatsu Adachi, Ryo Sakakibara, Takuya Imazu, Yoshiki Satake, Shouta Tokoro, Atsuo Nakazaki, Yuuki Ishikawa, Yusuke Sawayama, Minoru Isobe, Keiichi Konoki, Yukie Chiba, Mari Yotsu-Yamashita
    • Organizer
      The 2st International Symposium on Chemical Biology of Natural Products: Target ID and Regulation of Bioactivity
    • Place of Presentation
      Yokohama
    • Related Report
      2013 Research-status Report
  • [Presentation] MTM基の新しい脱保護法に関する研究2013

    • Author(s)
      橋本穂果、今津拓也、榊原 良、安立昌篤、西川俊夫
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      浜松
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthetic Studies on Tagetitoxin2013

    • Author(s)
      Hitomi Yamada, Masaatsu Adachi, Toshio Nishikawa
    • Organizer
      The 8th International Conference on Cutting-Edge Organic Chemistry in Asia and The 4th New Phase International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-8/NICCEOCA-4)
    • Place of Presentation
      Osaka
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthetic Studies on Nitrogen-Containing Natural Products2013

    • Author(s)
      Toshio Nishikawa, Masaatsu Adachi, Ryo Sakakibara, Shouta Tokoro, Takuya Imazu, Yoshiki Satake, Minoru Isobe
    • Organizer
      Pure and Applied Chemistry International Conference 2013
    • Place of Presentation
      Thailand
    • Related Report
      2012 Research-status Report
  • [Presentation] 植物毒素Tagetitoxinの合成研究2013

    • Author(s)
      山田ひと美、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      仙台
    • Related Report
      2012 Research-status Report
  • [Presentation] 5,11-ジデオキシテトロドトキシンの全合成2013

    • Author(s)
      今津拓也、安立昌篤、磯部 稔、西川俊夫
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      仙台
    • Related Report
      2012 Research-status Report
  • [Presentation] サブタイプ選択的Na+チャネル阻害剤創製を目指したテトロドトキシン類縁体の合成研究2012

    • Author(s)
      西川俊夫、安立昌篤、此木敬一
    • Organizer
      新学術領域研究「天然物ケミカルバイオロジー:分子標的と活性制御」第2回領域公開シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] インドールアルカロイド セスペンドールの合成研究2012

    • Author(s)
      樋口恵子、Nopporn Thasana、山田ひと美、杉野公美、中崎敦夫、安立昌篤、西川俊夫
    • Organizer
      第47回天然化学物談話会
    • Place of Presentation
      熊本
    • Related Report
      2012 Research-status Report
  • [Presentation] 5,11-ジデオキシテトロドトキシンの合成2012

    • Author(s)
      今津拓也、安立昌篤、西川俊夫
    • Organizer
      第47回天然化学物談話会
    • Place of Presentation
      熊本
    • Related Report
      2012 Research-status Report
  • [Presentation] ポリガロリド類縁体の合成研究2012

    • Author(s)
      松原真史、山田ひと美、安立昌篤、西川俊夫
    • Organizer
      第47回天然化学物談話会
    • Place of Presentation
      熊本
    • Related Report
      2012 Research-status Report
  • [Presentation] 植物毒素Tagetitoxinの合成研究2012

    • Author(s)
      山田ひと美、安立昌篤、西川俊夫
    • Organizer
      第29回有機合成化学セミナー
    • Place of Presentation
      静岡
    • Related Report
      2012 Research-status Report
  • [Presentation] インドールアルカロイド セスペンドールの合成研究2012

    • Author(s)
      樋口恵子、Nopporn Thasana、山田ひと美、杉野公美、中崎敦夫、安立昌篤、西川俊夫
    • Organizer
      名古屋大学博士課程教育リーディングプログラム グリーン自然科学国際教育研究プログラム 自然科学連携講座2(基礎生物学研究所)&リトリート研究所研修
    • Place of Presentation
      岡崎
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis of Marine Toxins Aiming at Developing Ion-Channel Inhibitors2012

    • Author(s)
      Toshio Nishikawa, Masaatsu Adachi, Ryo Sakakibara, Takuya Imazu, Yoshiki Satake, Minoru Isobe
    • Organizer
      The 1st International Symposium on Chemical Biology of Natural Products: Target ID and Regulation of Bioactivity
    • Place of Presentation
      Kyoto
    • Related Report
      2012 Research-status Report
  • [Presentation] Collective Synthesis of Tetrodotoxin and its Analogus2012

    • Author(s)
      Toshio Nishikawa, Masaatsu Adachi, Ryo Sakakibara, Shouta Tokoro, Takuya Imazu, Yoshiki Satake, Minoru Isobe
    • Organizer
      The 7th International Conference on Cutting-Edge Organic Chemistry in Asia and The 3rd New Phase International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Singapore
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthetic Studies on Sespendole

    • Author(s)
      Keiko Higuchi, Nopporn Thasana, Kumi Sugino, Atsuo Nakazaki, Masaatsu Adachi, Toshio Nishikawa
    • Organizer
      Thieme Chemistry - Nagoya Symposium 2013
    • Place of Presentation
      Nagoya
    • Related Report
      2013 Research-status Report
  • [Presentation] インドールアルカロイド セスペンドールの合成研究

    • Author(s)
      樋口恵子、Nopporn Thasana、杉野公美、中崎敦夫、安立昌篤、西川俊夫
    • Organizer
      名古屋大学博士課程教育リーディングプログラム グリーン自然科学国際教育研究プログラム 「企業研究者を志すための合成化学セミナー」
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] 多環式天然物の合成研究

    • Author(s)
      安立昌篤
    • Organizer
      天然物化学研究会「天然物化学の潮流を読む」
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Nav安定発現系の構築とTTX関連化合物の結合性評価

    • Author(s)
      千葉雪絵、長由扶子、安立昌篤、榊原 良、所 聖太、今津拓也、磯部 稔、西川俊夫、山下まり、此木敬一
    • Organizer
      日本農芸化学会東北支部第148回大会
    • Place of Presentation
      盛岡
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthetic Studies on Sespendole

    • Author(s)
      Keiko Higuchi, Nopporn Thasana, Kumi Sugino, Atsuo Nakazaki, Masaatsu Adachi, Toshio Nishikawa
    • Organizer
      名古屋大学博士課程教育リーディングプログラムリーディングプログラム 成果報告会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] 薬用植物由来の多環性天然物Polygalolide Aの全合成

    • Author(s)
      安立昌篤、山田ひと美、磯部 稔、西川俊夫
    • Organizer
      新学術領域研究「天然物ケミカルバイオロジー:分子標的と活性制御」第1回若手研究者ワークショップ
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] 5,11-ジデオキシテトロドトキシンの全合成

    • Author(s)
      今津拓也、安立昌篤、磯部 稔、西川俊夫
    • Organizer
      日本農芸化学会中部支部第165回例会
    • Place of Presentation
      名古屋
    • Related Report
      2012 Research-status Report
  • [Presentation] 植物毒素Tagetitoxinの合成研究

    • Author(s)
      山田ひと美、安立昌篤、西川俊夫
    • Organizer
      名古屋大学博士課程教育リーディングプログラムリーディングプログラム 成果報告会
    • Place of Presentation
      名古屋
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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