Indole/Azine C. H/C. H Coupling : Applications to Natural Products Synthesis

• Project/Area Number: 22750037
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Nagoya University
• Principal Investigator: YAMAGUCHI Junichiro 名古屋大学, 大学院・理学研究科, 助教 (00529026)
• Project Period (FY): 2010 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000); Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2010: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 合成有機化学 / インドール / 天然物 / ピリジン / クロスカップリング / 炭素-水素結合官能基化 / パラジウム触媒 / dragmacidin / eudistomin U / dragmacidin D

Research Abstract

We have developed a palladium-catalyzed C-H/C-H coupling reaction of indoles or pyrroles with azine N oxides. Furthermore, we have accomplished the synthesis of marine indole alkaloid dragmacidin D and eudistomin U by utilizing this newly developed C-H/C-H coupling reaction.

Research Products

• [Journal Article] Synthesis of Dragmacidin D via Direct C-H Couplings (2011)
  • Author(s): Mandal, D.; Yamaguchi, A. D.; Yamaguchi, J.; Itami, K.
  • Journal Title: J.Am.Chem.Soc. Volume: 133 Issue: 49 Pages: 19660-19660
  • DOI: 10.1021/ja209945x
  • Peer Reviewed
• [Journal Article] Synthesis of Bioactive Compounds through C-H Bond Functionalization (2011)
  • Author(s): Yamaguchi, J.; Itami, K.
  • Journal Title: Catalysts and Catalysis Volume: 53 Pages: 293-293
  • NAID: 10029500001
  • URL: http://www.shokubai.org/jnl/cgi-bin/cootw.cgi/5305029300h
  • Peer Reviewed
• [Journal Article] Oxidative C-H/C-H Coupling of Azine and Indole/Pyrrole Nuclei : Palladium Catalysis and Synthesis of Eudistomin U (2011)
  • Author(s): Yamaguchi, A. D.; Mandal, D.; Yamaguchi, J.; Itami, K.
  • Journal Title: Chem. Lett Volume: 40 Issue: 6 Pages: 555-555
  • DOI: 10.1246/cl.2011.555
  • NAID: 130004426229
  • Peer Reviewed
• [Journal Article] Oxidative Biaryl Coupling of Thiophenes and Thiazoles with Arylboronic Acids through Palladium Catalysis : Otherwise-Difficult C4-Selective C-H Arylation Enabled by Boronic Acids (2011)
  • Author(s): Kirchberg, S.; Tani, S.; Ueda, K.; Yamaguchi, J.; Studer, A.; Itami, K.
  • Journal Title: Angew. Chem. Int. Ed Volume: 50 Issue: 14 Pages: 2387-2387
  • DOI: 10.1002/anie.201007232
  • Peer Reviewed
• [Journal Article] Oxidative C-H/C-H Coupling of Azine and Indole/Pyrrole Nuclei : Palladium Catalysis and Synthesis of Eudistomin U (2011)
  • Author(s): 山口敦史
  • Journal Title: Chem.Lett. Volume: 40 Pages: 555557-555557
  • NAID: 10028243360
  • Peer Reviewed
• [Journal Article] Synthesis of Bioactive Compounds through C-H Bond Functionalization (2011)
  • Author(s): 山口潤一郎
  • Journal Title: Catalysts & Catalysis Volume: 53 Pages: 293298-293298
  • NAID: 10029500001
  • Peer Reviewed
• [Journal Article] Oxidative Biaryl Coupling of Thiophenes and Thiazoles with Arylboronic Acids through Palladium Catalysis : Otherwise-Difficult C4-Selective C-H Arylation Enabled by Boronic Acids (2011)
  • Author(s): キルシュベーグジルビア
  • Journal Title: Angew.Chem.Int.Ed. Volume: 50 Pages: 2387-2391
  • Peer Reviewed
• [Journal Article] A General Catalyst for the/3-Selective C-H Bond Arylation of Thiophenes with Iodoarenes (2010)
  • Author(s): Ueda, K. Yanagisawa, S.; Yamaguchi, J.; Itami, K.
  • Journal Title: Angew. Chem. Int. Ed Volume: 49 Issue: 47 Pages: 8946-8946
  • DOI: 10.1002/anie.201005082
  • Peer Reviewed
• [Journal Article] A General Catalyst for the β-Selective C-H Bond Arylation of Thiophenes with Iodoarenes (2010)
  • Author(s): 植田桐加
  • Journal Title: Angew.Chem.Int.Ed. Volume: 49 Pages: 8946-8949
  • Peer Reviewed
• [Presentation] 芳香環連結反応を鍵とした生物活性化合物の迅速合成 (2012)
  • Author(s): 山口潤一郎
  • Organizer: 第26回若い世代の特別講演会
  • Place of Presentation: 慶応大学(横浜)
  • Year and Date: 2012-03-27
• [Presentation] 芳香環連結反応を鍵とした生物活性化合物の迅速合成 (2012)
  • Author(s): 山口潤一郎
  • Organizer: 第26回若い世代の特別講演会
  • Place of Presentation: 慶応大学(横浜)(招待講演)
  • Year and Date: 2012-03-27
• [Presentation] Synthesis of Biologically Active Compounds via Direct Arene Assembling Reaction (2012)
  • Author(s): 山口潤一郎
  • Place of Presentation: 東京
  • Year and Date: 2012-03-21
• [Presentation] 自在芳香環直接連結反応が拓く合成戦略 (2011)
  • Author(s): 山口潤一郎
  • Organizer: 有機合成総合講演会
  • Place of Presentation: 静岡県立大学(静岡)
  • Year and Date: 2011-12-17
• [Presentation] 自在芳香環直接連結反応が拓く合成戦略 (2011)
  • Author(s): 山口潤一郎
  • Organizer: 有機合成総合講演会
  • Place of Presentation: 静岡県立大学(静岡)(招待講演)
  • Year and Date: 2011-12-17
• [Presentation] Synthesis of Dragmacidin D via Direct C-H Couplings (2011)
  • Author(s): Junichiro Yamaguchi
  • Organizer: The 12th IRTG JOINT SYMPOSIUM
  • Year and Date: 2011-10-03
• [Presentation] Synthesis of Dragmacidin D via Direct C-H Couplings (2011)
  • Author(s): 山口潤一郎
  • Organizer: The 12th IRTG JOINT SYMPOSIUM
  • Place of Presentation: 名古屋大学(愛知)
  • Year and Date: 2011-10-03
• [Presentation] C-Hアリール化反応を駆使したdragmacidin Dの全合成 (2011)
  • Author(s): 山口潤一郎・マンダルデバシス・山口敦史・伊丹健一郎
  • Organizer: 第53回天然有機化合物討論会0-45
  • Place of Presentation: 大阪(国内)
  • Year and Date: 2011-09-27
• [Presentation] C-Hアリール化反応を駆使したdragmacidin Dの全合成 (2011)
  • Author(s): 山口潤一郎
  • Organizer: 第53回天然有機化合物討論会
  • Place of Presentation: 大阪国際交流センター(大阪)
  • Year and Date: 2011-09-27
• [Presentation] 炭素一水素結合直接アリール化反応を鍵とするdragmacidin Dの全合成 (2011)
  • Author(s): 山口潤一郎・マンダルデバシス・山口敦史・伊丹健一郎
  • Organizer: 第58回有機金属化学討論会02-14
  • Place of Presentation: 名古屋(国内)
  • Year and Date: 2011-09-08
• [Presentation] 炭素-水素結合直接アリール化反応を鍵とするdragmacidin Dの全合成 (2011)
  • Author(s): 山口潤一郎
  • Organizer: 第58回有機金属化学討論会
  • Place of Presentation: 名古屋大学(愛知)
  • Year and Date: 2011-09-08
• [Presentation] 芳香環直接連結反応を駆使した生物活性物質の合成研究 (2011)
  • Author(s): 山口潤一郎
  • Organizer: 第46回天然物化学談話会
  • Place of Presentation: 静岡
  • Year and Date: 2011-07-08
• [Presentation] 芳香環直接連結反応を駆使した生物活性物質の合成研究 (2011)
  • Author(s): 山口潤一郎
  • Organizer: 第46回天然物化学談話会
  • Place of Presentation: 熱川ハイツ(静岡)
  • Year and Date: 2011-07-08
• [Presentation] Synthesis of Biologically Active Compounds via Direct Arene-Assembling Reaction (2011)
  • Author(s): Junichiro Yamaguchi
  • Organizer: Nagoya Symposium of Green Synthesis & Catalysis
  • Place of Presentation: 名古屋大学(愛知)
  • Year and Date: 2011-03-13
• [Presentation] Indole-azine C-H/C-Hcoupling for natural product synthesis (2010)
  • Author(s): Debashis Mandal, Atsushi D. Yamaguchi, Junichiro Yamaguchi, and Kenichiro Itami
  • Organizer: The International Chemical Congress of Pacific Basin Societies(Pacifichem 2010)
  • Place of Presentation: Honolulu, USA
  • Year and Date: 2010-12-20
• [Presentation] Indole-azine C-H/C-H coupling for natural product synthesis (2010)
  • Author(s): 山口潤一郎
  • Organizer: The International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)
  • Place of Presentation: ホノルル(米国)
  • Year and Date: 2010-12-20
• [Presentation] Synthesis of dragmacidin D via direct C-H bond arylation (2010)
  • Author(s): Yamaguchi, J.; Mandal D.; Yamaguchi, A. D.; Ueda, K.; Itami, K
  • Organizer: The International Chemical Congress of Pacific Basin Societies(Pacifichem 2010)
  • Place of Presentation: Honolulu, USA
  • Year and Date: 2010-12-18
• [Presentation] 自在芳香環直接連結反応が拓く合成戦略 (2010)
  • Author(s): 山口潤一郎
  • Organizer: 名古屋市立大学薬学部第117回薬学談話会
  • Place of Presentation: 愛知
  • Year and Date: 2010-11-17
• [Presentation] 自在芳香環直接連結反応が拓く合成戦略 (2010)
  • Author(s): 山口潤一郎
  • Organizer: 名古屋市立大学薬学部第117回薬学談話会
  • Place of Presentation: 名古屋市立大学(愛知)
  • Year and Date: 2010-11-17
• [Presentation] 標的指向型芳香環直接連結反応の開発と展開 (2010)
  • Author(s): 山口潤一郎
  • Organizer: 帝人ファーマ株式会社
  • Place of Presentation: 東京
  • Year and Date: 2010-06-23
• [Presentation] 標的指向型芳香環直接連結反応の開発と展開 (2010)
  • Author(s): 山口潤一郎
  • Organizer: 帝人ファーマ株式会社特別講演会
  • Place of Presentation: 帝人ファーマ株式会社(東京)
  • Year and Date: 2010-06-23
• [Patent(Industrial Property Rights)] 含窒素複素環化合物及びその製造方法 (2010)
  • Inventor(s): 伊丹健一郎、山口潤一郎、デバシスマンダル、山口敦史
  • Industrial Property Rights Holder: 伊丹健一郎、山口潤一郎、デバシスマンダル、山口敦史
  • Industrial Property Number: 2010-046887
  • Filing Date: 2010-03-03
  • Acquisition Date: 2011-09-15