Development of efficient synthetic method of functionalized carbocycles and synthetic study of resiniferatoxin

• Project/Area Number: 20890043
• Research Category: Grant-in-Aid for Young Scientists (Start-up)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: The University of Tokyo
• Principal Investigator: URABE Daisuke The University of Tokyo, 大学院・薬学系研究科, 助教 (80503515)
• Project Period (FY): 2008 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥2,925,000 (Direct Cost: ¥2,250,000、Indirect Cost: ¥675,000); Fiscal Year 2009: ¥1,365,000 (Direct Cost: ¥1,050,000、Indirect Cost: ¥315,000); Fiscal Year 2008: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
• Keywords: 炭素環 / ラジカル反応 / 天然物合成 / テルペン / Diels Alder反応 / 炭素環構築 / Diels-Alder反応 / ラジカル / ジテルペン / 生理活性物質 / 全合成 / O, S-アセタール

Research Abstract

An efficient radical cyclization from alkoxy selenoacetals, prepared by seleno pummerer reaction, was successfully developed to provide functionalized carbocycles. Toward a total synthesis of resiniferatoxin featured by the radical reaction, an advanced intermediate was synthesized from the quinone derivative through Diels-Alder reaction.

Research Products

• [Journal Article] New Syntheses of E7389 C14-35 and Halichondrin C14-C38 Building Blocks : Reductive Cyclization and Oxy-Michael Cyclization Approaches (2009)
  • Author(s): Dong, C.-G., Henderson, J. A., Kaburagi, Y., Sasaki, T., Kim, D.-S., Kim, J. T., Urabe, D., Guo, H., Kishi, Y.
  • Journal Title: Journal of the American Chemical Society 131 Pages: 15642-15646
  • Peer Reviewed
• [Journal Article] Toolbox Approach to the Search for Effective Ligands for Catalytic Asymmetric Cr-Mediated Coupling Reactions (2009)
  • Author(s): Guo, H., Dong, C.-G., Kim, D.-S., Urabe, D., Wang, J., Kim. J. T., Liu, X., Sasaki, T., Kishi, Y.
  • Journal Title: Journal of the American Chemical Society 131 Pages: 15387-15393
  • Peer Reviewed
• [Journal Article] Total Synthesis and Bioactivity of Resolvin E2 (2009)
  • Author(s): Ogawa, S., Urabe, D., Yokokura, Y., Arai, H., Arita, M., Inoue, M.
  • Journal Title: Organic Letters 11 Pages: 3602-3605
  • Peer Reviewed
• [Journal Article] Total Syntheses of Sesquiterpenes from Illicium Species (2009)
  • Author(s): Urabe, D., Inoue, M.
  • Journal Title: Tetrahedron 65 Pages: 6271-6289
  • Peer Reviewed
• [Journal Article] Syntheses of N-Acylisoxazolidine Derivatives, Related to a Partial Structure Found in Zetekitoxin AB, a Golden Frog Poison (2009)
  • Author(s): Nishikawa, T., Urabe, D., Isobe, M.
  • Journal Title: Heterocycles 79 Pages: 379-385
  • NAID: 40016543072
  • Peer Reviewed
• [Journal Article] New Syntheses of E7389 C14-35 and Halichondrin C14-C38 Building Blocks : Reductive Cyclization and Oxy-Michael Cyclization Approaches. (2009)
  • Author(s): Dong, C.-G; Henderson, J.A.; Kaburagi, Y.; Sasaki, T.; Kim, D.-S.; Kim, J.T.; Urabe, D.; Guo, H.; Kishi, Y.
  • Journal Title: Journal of the American Chemical Society 131 Pages: 15642-15646
  • Peer Reviewed
• [Journal Article] Toolbox Approach to the Search for Effective Ligands for Catalytic Asymmetric Cr-Mediated Coupling Reactions. (2009)
  • Author(s): Guo, H.; Dong, C.-G; Kim, D.-S.; Urabe.D.; Wang, J.; Kim.J.T.; Liu, X.; Sasaki, T.; Kishi, Y.
  • Journal Title: Journal of the American Chemical Society 131 Pages: 15387-15393
  • Peer Reviewed
• [Journal Article] Total Synthesis and Bioactivity of Resolvin E2. (2009)
  • Author(s): Ogawa, S.; Urabe, D.; Yokokura, Y.; Arai, H.; Arita, M.; Inoue, M.
  • Journal Title: Organic Letters 11 Pages: 3602-3605
  • Peer Reviewed
• [Journal Article] Total Syntheses of Sesquiterpenes from Illicium Species. (2009)
  • Author(s): Urabe, D.; Inoue, M.
  • Journal Title: Tetrahedron 65 Pages: 6271-6289
  • Peer Reviewed
• [Journal Article] Syntheses of N-Acyisoxazolidine Derivatives, Related to a Partial Structure Found in Zetekitoxin AB, a Golden Frog Poison (2009)
  • Author(s): Toshio, Nishikawa, Daisuke Urabe, and Minoru, Isobe
  • Journal Title: Heteocycles 79 Pages: 379-385
  • Peer Reviewed
• [Presentation] リアノジンの合成研究 (2010)
  • Author(s): 長友優典, 占部大介, 井上将行
  • Organizer: 第130回日本薬学会年会
  • Place of Presentation: 岡山
  • Year and Date: 2010-03-30
• [Presentation] Hyponine Bの全合成研究 (2010)
  • Author(s): 石山備凡, 占部大介, 井上将行
  • Organizer: 第130回日本薬学会年会
  • Place of Presentation: 岡山
  • Year and Date: 2010-03-30
• [Presentation] レジニフェラトキシンの合成研究 (2010)
  • Author(s): 村井耕一, 占部大介, 井上将行
  • Organizer: 第130回日本薬学会年会
  • Place of Presentation: 岡山
  • Year and Date: 2010-03-30
• [Presentation] アガロフラン骨格を有するセスキテルペンの合成研究 (2010)
  • Author(s): 岩津理史, 占部大介, 井上将行
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 東大阪
  • Year and Date: 2010-03-28
• [Presentation] ウアバインの合成研究 (2010)
  • Author(s): 粕谷智史, 占部大介, 井上将行
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 東大阪
  • Year and Date: 2010-03-28
• [Presentation] アガロフラン骨格を有するセスキテルペンの合成研究 (2009)
  • Author(s): 岩津理史, 占部大介, 井上将行
  • Organizer: 第35回反応と合成の進歩シンポジウム
  • Place of Presentation: 金沢
  • Year and Date: 2009-11-17
• [Presentation] Efficient construction of carbocycles using O,Se-acetals as key intermediates (2009)
  • Author(s): 占部大介, 染谷あゆみ, 井上将行
  • Organizer: 第26回有機合成化学セミナー
  • Place of Presentation: 前橋
  • Year and Date: 2009-09-16
• [Presentation] ウアバインの合成研究 (2009)
  • Author(s): 粕谷智史, 占部大介, 井上将行
  • Organizer: 第26回有機合成化学セミナー
  • Place of Presentation: 前橋
  • Year and Date: 2009-09-16
• [Presentation] Efficient construction of carbocycles using O,Se-acetals as key intermediates (2009)
  • Author(s): 占部大介, 井上将行
  • Organizer: 第5回日韓天然物化学談話会
  • Place of Presentation: 湯河原
  • Year and Date: 2009-08-27
• [Presentation] Hyponine Bの合成研究 (2009)
  • Author(s): 石山備凡, 占部大介, 井上将行
  • Organizer: 第44回天然物化学談話会
  • Place of Presentation: 筑波
  • Year and Date: 2009-07-08
• [Presentation] レジニフェラトキシンの合成研究 (2009)
  • Author(s): 村井耕一, 占部大介, 井上将行
  • Organizer: 第57回有機合成化学協会関東支部シンポジウム
  • Place of Presentation: 東京
  • Year and Date: 2009-05-09
• [Presentation] O,S-アセタールを鍵中間体とする炭素骨格構築法の開発 (2009)
  • Author(s): 染谷あゆみ, 占部大介, 井上将行
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
  • Year and Date: 2009-03-27
• [Presentation] Hyponine Bの合成研究 (2009)
  • Author(s): 石山備凡, 占部大介, 井上将行
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
  • Year and Date: 2009-03-27
• [Presentation] アガロフラン骨格を有するセスキテルペンの全合成研究 (2009)
  • Author(s): 岩津理史, 占部大介, 井上将行
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
  • Year and Date: 2009-03-27
• [Presentation] O, S-アセタールを鍵中間体とする炭素骨格構築法の開発 (2009)
  • Author(s): 染谷あゆみ, 占部大介, 井上将行
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
  • Year and Date: 2009-03-27
• [Presentation] HyponineBの合成研究 (2009)
  • Author(s): 石山備凡, 占部大介, 井上将行
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
  • Year and Date: 2009-03-27
• [Presentation] リアノジンの合成研究 (2008)
  • Author(s): 萩原幸司, 岩津理史, 金野大助, 友田修司, 占部大介, 井上将行
  • Organizer: 第94回有機合成シンポジウム
  • Place of Presentation: 東京
  • Year and Date: 2008-11-07