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Stereocontrolled Synthesis of nitrogen-containing polycyclic scaffolds using axially chiral ortho-azaxylylene intermediate

Research Project

Project/Area Number 25450151
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

NAKAZAKI Atsuo  名古屋大学, 生命農学研究科, 准教授 (00366428)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsortho-アザキシリレン / 含窒素化合物 / 不斉合成 / 立体制御 / 3,3-二置換オキシインドール / 軸不斉
Outline of Final Research Achievements

In this study, we explored two issues for the synthesis of nitrogen-containing polycyclic natural products: 1) stereoselective synthesis of 3,3-disubstituted oxindoles having a C3-quaternary stereogenic center via a chiral ortho-azaxylylene intermediate, and 2) catalytic asymmetric synthesis of N-aryl isatin. Our result allows us to synthesize a wide variety of oxindoles having substituents which can be seen in polycyclic alkaloids.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (50 results)

All 2016 2015 2014 2013 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results,  Open Access: 1 results) Presentation (40 results)

  • [Journal Article] Diastereoselective Synthesis of 3,3-Disubstituted Oxindoles from N-Aryl-3-Chlorooxindoles Bearing Axial Chirality via Nucleophilic Substitution.2015

    • Author(s)
      Nakazaki, A.; Miyagawa, K.; Nishikawa, T.
    • Journal Title

      Synlett

      Volume: 26 Issue: 08 Pages: 0-0

    • DOI

      10.1055/s-0034-1380266

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 1.5-dioxaspiro[3.4]octane through bromocation-induced cascade cyclization.2015

    • Author(s)
      Nakazaki, A.; Nakane, Y.; Ishikawa, Y.; Nishikawa, T.
    • Journal Title

      Heterocycles

      Volume: 91 Issue: 6 Pages: 1157-1163

    • DOI

      10.3987/com-15-13208

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a C-N Axially Chiral N-Aryl Isatin through Asymmetric Intramolecular N-Arylation.2015

    • Author(s)
      Nakazaki, A.; Miyagawa, K.; Miyata, N.; Nishikawa, T.
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 21 Issue: 21 Pages: 4603-4606

    • DOI

      10.1002/ejoc.201500593

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Unexpected Metal-Free Transformation of gem-Dibromomethylenes to Ketones under Acetylation Conditions.2015

    • Author(s)
      Kimura, R.; Sawayama, Y.; Nakazaki, A.; Miyamoto, K.; Uchiyama, M.; Nishikawa, T.
    • Journal Title

      Chem. Asian J.

      Volume: 10 Issue: 4 Pages: 1035-1041

    • DOI

      10.1002/asia.201403277

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Multimodal Biopanning of T7 Phage-displayed Peptide Reveals Angiomotin as a Potential Receptor of an Anti-angiogenic Macrolide Roxithromycin2015

    • Author(s)
      Takakusagi, K.; Takakusagi, Y.; Suzuki, T. Toizaki, A.; Suzuki, A.; Kawakatsu, Y.; Watanabe, M.; Saito, Y.; Fukuda, R.; Nakazaki, A.; Kobayashi, S.; Sakaguchi, K.; Sugawara, F.
    • Journal Title

      Eur. J. Med. Chem.

      Volume: 90 Pages: 809-821

    • DOI

      10.1016/j.ejmech.2014.12.015

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthetic study of spiroiridal triterpenoids: construction of functionalized spiro[4.5]decane skeleton using Claisen rearrangement of 2-(alkenyl)dihydropyran2015

    • Author(s)
      Takanashi, T.; Tamura, K.; Suzuki, T.; Nakazaki, A.; Kobayashi, S.
    • Journal Title

      Tetrahedron Lett.

      Volume: 56 Issue: 2 Pages: 327-330

    • DOI

      10.1016/j.tetlet.2014.11.078

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of crambescin B carboxylic acid, a potent inhibitor of voltage-gated sodium channel.2014

    • Author(s)
      Nakazaki, A.; Ishikawa, Y.; Sawayama, Y.; Yotsu-Yamashita, M.; Nishikawa, T.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 12 Issue: 1 Pages: 53-56

    • DOI

      10.1039/c3ob42017e

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis of spirocyclic oxindoles based on a one-pot Ullmann coupling/Claisen rearrangement and its application to the synthesis of a hexahydropyrrolo[2,3-b]indole alkaloid2013

    • Author(s)
      Miyamoto, H.; Hirano, T.; Okawa, Y.; Nakazaki, A.; Kobayashi, S.
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 45 Pages: 9481-9493

    • DOI

      10.1016/j.tet.2013.08.057

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Structural Study on a Naturally Occurring Terphenyl Quinone2013

    • Author(s)
      Nakazaki, A.; Huang, W.-Y.; Koga, K.; Yingyongnarongkul, B.; Boonsombat, J.; Sawayama, Y.; Tsujimoto, T.; Nishikawa, T.
    • Journal Title

      Bioscience, Biotechnology, and Biochemistry

      Volume: 77 Issue: 7 Pages: 1529-1532

    • DOI

      10.1271/bbb.130199

    • NAID

      10031190464

    • ISSN
      0916-8451, 1347-6947
    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Deprotection of the Methoxymethyl Group on 3-Spiro-2-oxindole under Basic Conditions2013

    • Author(s)
      Nakazaki, A.; Iwakiri, K.; Hirano, T.; Suzuki, T.; Kobayashi, S.
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 61 Issue: 5 Pages: 587-591

    • DOI

      10.1248/cpb.c13-00068

    • NAID

      130003360776

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthetic Study on Lycojapodine A2016

    • Author(s)
      Wen-Yu Huang, Toshio Nishikawa, Atsuo Nakazaki
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌
    • Year and Date
      2016-03-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] Inagami-Tamura EDLFの合成化学的研究: 光学活性体の合成ルートの確立2016

    • Author(s)
      橋本圭古、池田 藍、西川俊夫、中崎敦夫
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌
    • Year and Date
      2016-03-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] (+)-サキシトキシンの合成研究2016

    • Author(s)
      上野壮平、中崎敦夫、西川俊夫
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京都
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthetic study on (+)-saxitoxin2016

    • Author(s)
      Sohei Ueno, Atsuo Nakazaki, 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 グリーン自然科学国際教育研究プログラム 年次報告会2015
    • Place of Presentation
      名古屋
    • Year and Date
      2016-01-08
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis of biologically active steroid-derived compounds from an edible mushroom2015

    • Author(s)
      Toshio Nishikawa, Yoshiki Nakane, Atsuo Nakazaki, Takuya Imazu, Shouta Tokoro, Ryo Sakakibara, Masaatsu Adachi, Keiichi Konoki, Mari Yotsu-Yamashita
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis and biological activities of guanidine-containing natural products2015

    • Author(s)
      Toshio Nishikawa, Yoshiki Nakane, Atsuo Nakazaki, Takuya Imazu, Shouta Tokoro, Ryo Sakakibara, Masaatsu Adachi, Keiichi Konoki, Mari Yotsu-Yamashita
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] Asymmetric synthesis of crambescin B carboxylic acid, a potent inhibitor of voltage-gated sodium channels, and its analogues2015

    • Author(s)
      Yoshiki Nakane, Yuki Ishikawa, Atsuo Nakazaki, Toshio Nishikawa
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] 電位依存性ナトリウムチャネルに対するテトロドトキシンおよび類縁体の活性阻害評価2015

    • Author(s)
      塚本匡顕、千葉雪絵、長 由扶子、安立昌篤、榊原 良、所 聖太、今津拓也、中崎敦夫、石川裕生、西川俊夫、山下まり、此木敬一
    • Organizer
      日本農芸化学会東北支部第150回大会
    • Place of Presentation
      仙台
    • Year and Date
      2015-10-03
    • Related Report
      2015 Annual Research Report
  • [Presentation] Inagami-Tamura EDLF (Endogenous Digitalis-Like Factor) の合成化学的研究2015

    • Author(s)
      橋本圭古、池田 藍、西川俊夫、中崎敦夫
    • Organizer
      2015年度日本農芸化学会中部・関西支部合同大会
    • Place of Presentation
      富山
    • Year and Date
      2015-09-19
    • Related Report
      2015 Annual Research Report
  • [Presentation] (+)-サキシトキシンの合成研究2015

    • Author(s)
      上野壮平、中崎敦夫、西川俊夫
    • Organizer
      第32回有機合成化学セミナー
    • Place of Presentation
      湯河原
    • Year and Date
      2015-09-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] クランベシンBカルボン酸とその誘導体の合成研究2015

    • Author(s)
      中根嘉祈、中崎敦夫、石川裕生、澤山裕介、山下まり、西川俊夫
    • Organizer
      第57回天然有機化合物討論会
    • Place of Presentation
      横浜
    • Year and Date
      2015-09-09
    • Related Report
      2015 Annual Research Report
  • [Presentation] ナトリウムチャネル阻害剤の創製を目指したグアニジン系天然物の合成2015

    • Author(s)
      (3)西川俊夫、中崎敦夫、中根嘉祈、石川裕生、安立昌篤、橋本穂果、今津拓也、所聖太、榊原良、此木敬一、千葉雪絵、山下まり
    • Organizer
      日本ケミカルバイオロジー学会 第10回年会
    • Place of Presentation
      仙台
    • Year and Date
      2015-06-10
    • Related Report
      2015 Annual Research Report
  • [Presentation] Crambescin B カルボン酸とその誘導体の不斉合成と生物活性評価2015

    • Author(s)
      中根嘉祈、中崎敦夫、石川裕生、澤山裕介、山下まり、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7回若手研究者ワークショップ
    • Place of Presentation
      仙台
    • Year and Date
      2015-06-09
    • Related Report
      2015 Annual Research Report
  • [Presentation] 天然グアニジン化合物を基盤としたイオンチャネル阻害剤の開発2015

    • Author(s)
      西川俊夫、中崎敦夫、安立昌篤、此木敬一、山下まり
    • Organizer
      天然物ケミカルバイオロジー~分子標的と活性制御~ 第8回公開シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2015-06-08
    • Related Report
      2015 Annual Research Report
  • [Presentation] 分子内不斉N-アリール化を利用したC-N軸性キラリティを有するオキシインドールの合成2015

    • Author(s)
      宮川敬太朗、西川俊夫、中崎敦夫
    • 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 Research-status Report
  • [Presentation] クランベシンBカルボン酸とその誘導体の不斉合成2015

    • Author(s)
      中根嘉祈、中崎敦夫、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 Research-status 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 Research-status Report
  • [Presentation] Synthetic studies on (+)-saxitoxin2014

    • Author(s)
      Sohei Ueno, Atsuo Nakazaki, 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 グリーン自然科学国際教育研究プログラム 年次報告会2014
    • Place of Presentation
      名古屋
    • Year and Date
      2014-12-18
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthetic Study on Lycojapodine A2014

    • Author(s)
      Wen-Yu Huang, Toshio Nishikawa, Atsuo Nakazaki
    • 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 年次報告会2014
    • Place of Presentation
      名古屋
    • Year and Date
      2014-12-18
    • Related Report
      2014 Research-status Report
  • [Presentation] Stereocontrolled asymmetric synthesis of crambescin B carboxylic acid, a potent inhibitor of voltage-gated sodium channels2014

    • Author(s)
      Atsuo Nakazaki, Yoshiki Nakane, Yuki Ishikawa, Yusuke Sawayama and Toshio Nishikawa
    • Organizer
      The 9th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-9)/ The 5th New Phase International Conference on Cutting-Edge Organic Chemistry in Asia (NICCEOCA-5)
    • Place of Presentation
      Petaling Jaya, Malaysia
    • Year and Date
      2014-12-01 – 2014-12-05
    • Related Report
      2014 Research-status Report
  • [Presentation] gem-ジブロモメチレンのケトンへの新奇変換反応2014

    • Author(s)
      木村梨乃、澤山裕介、中崎敦夫、西川俊夫
    • Organizer
      第106回有機合成シンポジウム2014年【秋】
    • Place of Presentation
      東京
    • Year and Date
      2014-11-06 – 2014-11-07
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthetic Study on Lycojapodine A2014

    • Author(s)
      Wen-Yu Huang, Toshio Nishikawa, Atsuo Nakazaki
    • 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 Research-status Report
  • [Presentation] (+)-saxitoxinの合成研究2014

    • Author(s)
      上野壮平、中崎敦夫、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 Research-status Report
  • [Presentation] 光学活性体クランベシンBカルボン酸の合成研究2014

    • Author(s)
      中根嘉祈、中崎敦夫、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 Research-status Report
  • [Presentation] Asymmetric Synthesis of Crambescin B Caroxylic Acid, A Potent Inhibitor of Voltage-Gated Sodium Channels2014

    • Author(s)
      Yoshiki Nakane, Atsuo Nakazaki, Yuki Ishikawa, Yusuke Sawayama, Toshio Nishikawa
    • Organizer
      IGER international Symposium on Chemical Science in Asia
    • Place of Presentation
      名古屋
    • Year and Date
      2014-05-26 – 2014-05-28
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthetic Study on Lycojapodine A2014

    • Author(s)
      Wen-Yu Huang, Atsuo Nakazaki, Toshio Nishikawa
    • 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] サキシトキシン骨格の新規構築法の開発2014

    • Author(s)
      上野壮平、中崎敦夫、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] 軸不斉を有するortho-アザキシリレン中間体を利用した3,3-二置換オキシインドールの立体選択的合成2013

    • Author(s)
      宮川敬太朗、西川俊夫、中崎敦夫
    • 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] カスケード型ブロモ環化反応を用いたサキシトキシン骨格の効率的構築法の開発2013

    • Author(s)
      上野壮平、中崎敦夫、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] 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 2nd 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] Crambescin Bカルボン酸の合成2013

    • Author(s)
      石川裕生、澤山裕介、中崎敦夫、西川俊夫
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      岐阜
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthetic Studies toward ent-Pactamycin2013

    • Author(s)
      Nobuyuki Matsumoto, Atsuo Nakazaki, Toshio Nishikawa
    • Organizer
      13th International Conference on the Chemistry of Antibiotics and Other Bioactive Compounds (ICCA-13)
    • Place of Presentation
      Yamanashi
    • 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] イオンチャネル阻害剤の合成研究2013

    • Author(s)
      西川俊夫、中崎敦夫、石川裕生、澤山裕介
    • Organizer
      新学術領域研究(研究領域提案型)天然物ケミカルバイオロジー~分子標的と活性制御~第4回公開シンポジウム
    • Place of Presentation
      つくば
    • 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] cis-縮環を有する多環式骨格の立体選択的構築

    • Author(s)
      池田 藍、中崎敦夫、西川俊夫
    • Organizer
      日本農芸化学会中部支部第168回例会
    • Place of Presentation
      名古屋
    • 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] Synthetic studies toward saxitoxin skeleton by a cascade cyclization reaction

    • Author(s)
      Sohei Ueno, Atsuo Nakazaki, Toshio Nishikawa
    • Organizer
      Thieme Chemistry - Nagoya Symposium 2013
    • Place of Presentation
      Nagoya
    • 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
      Thieme Chemistry - Nagoya Symposium 2013
    • Place of Presentation
      Nagoya
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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