New method for the construction of bicyclic products by using multiple bonds

• Project/Area Number: 24790009
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Kanazawa University
• Principal Investigator: INAGAKI Fuyuhiko 金沢大学, 薬学系, 准教授 (80506816)
• Project Period (FY): 2012-04-01 – 2014-03-31
• Project Status: Completed (Fiscal Year 2013)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000); Fiscal Year 2012: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
• Keywords: アレン / ロジウム / 環化反応 / ニ環性化合物

Research Abstract

We found that 1) Diels-Alder reaction of dienophile and exo-dimethylene derived from the cycloisomerization of bisallene provided the bicyclo[[m.4.0] derivatives (m=6,7), 2) Rh(I)-catalyzed cycloisomerization of alkene-substituted allenylcyclopropanes gave bicyclo[4.3.0]nonadienes stereoselectively, and 3) Rh(I)-catalyzed intramolecular [5+2-2] cycloadditions of allene-allenylcyclopropane formed the bicycle[5.3.0] derivatives.

Research Products

• [Journal Article] [2+2+1] Cyclization in allenes (2014)
  • Author(s): S. Kitagaki, F. Inagaki, C. Mukai
  • Journal Title: Chem. Soc. Rev. Volume: 43 Issue: 9 Pages: 2956-2978
  • DOI: 10.1039/c3cs60382b
  • Peer Reviewed
• [Journal Article] Rh(I)-Catalyzed Intramolecular Carbonylative [2+2+1] Cycloaddition Reaction: Preparation of Bicyclo[5.3.0]decadienones with Substituted Cyclopentenone Frameworks (2014)
  • Author(s): Mukai, C.; Takahashi, Y.; Ogawa, K.; Hayashi, Y.; Inagaki, F.
  • Journal Title: Chemical and Pharmaceutical Bulletin Volume: 62 Issue: 1 Pages: 84-87
  • DOI: 10.1248/cpb.c13-00711
  • NAID: 130003381812
  • ISSN: 0009-2363, 1347-5223
  • Peer Reviewed
• [Journal Article] Characterization and functionality of immidazolium ionic liquids modified magnetic nanoparticles (2013)
  • Author(s): Li, Y., Tang, N., Inagaki, F., Mukai, C., Hayakawa, K
  • Journal Title: J. Chem Volume: 861021 Issue: 1 Pages: 7-7
  • DOI: 10.1155/2013/861021
  • NAID: 120005302296
  • Peer Reviewed
• [Journal Article] Rhodium(I)-Catalyzed Cycloisomerization of Alkene-Substituted Allenylcyclopropanes: Stereoselective Formation of Bicyclo[4.3.0]nonadienes (2013)
  • Author(s): K. Sugikubo, F. Omachi, Y. Miyanaga, F. Inagaki, C. Matsumoto, C. Mukai
  • Journal Title: Angew. Chem. Int. Ed. Volume: 52 Issue: 43 Pages: 11369-11372
  • DOI: 10.1002/anie.201305958
  • Peer Reviewed
• [Journal Article] Progress in Carbonylative [2+2+1] Cycloaddition: Utilization of a Nitrile Group as the π Component (2013)
  • Author(s): T. Iwata, F. Inagaki, C. Mukai
  • Journal Title: Angew. Chem. Int. Ed. Volume: 52 Issue: 42 Pages: 11138-11142
  • DOI: 10.1002/anie.201305729
  • Peer Reviewed
• [Journal Article] Cyclopropanes in Nicholas reaction: formation of spiroketals with a five-membered and a seven- of eight-membered ring (2013)
  • Author(s): C. Mukai, T. Kojima, T. Kawamura, F. Inagaki
  • Journal Title: Tetrahedron Volume: 69 Issue: 36 Pages: 7659-7669
  • DOI: 10.1016/j.tet.2013.05.056
  • Peer Reviewed
• [Journal Article] Histidine augments the suppression of hepatic glucose production by central insulin action. (2013)
  • Author(s): Kimura K, Nakamura Y, Inaba Y, Matsumoto M, Kido Y, Asahara S, Matsuda T, Watanabe H, Maeda A, Inagaki F, Mukai C, Takeda K, Akira S, Ota T, Nakabayashi H, Kaneko S, Kasuga M, Inoue H.
  • Journal Title: Diabetes Volume: 62 Issue: 7 Pages: 2266-77
  • DOI: 10.2337/db12-1701
  • Peer Reviewed
• [Journal Article] Total Syntheses of (±)-Fawcettimine, (±)-Fawcettidine, (±-Lycoflexine and (±) -Lycoposerramine- Q (2013)
  • Author(s): N. Itoh
  • Journal Title: Chem. Eur. J. Volume: (in press) Issue: 26 Pages: 8665-8672
  • DOI: 10.1002/chem.201300364
  • Peer Reviewed
• [Journal Article] Syntheses of 6-8-5 tricyclic ring systems by carbonylative[2+2+1]cycloaddition of bis(allene)s (2013)
  • Author(s): M. T. S. Shafawati
  • Journal Title: Tetrahedron Volume: 69 Issue: 5 Pages: 1509-1515
  • DOI: 10.1016/j.tet.2012.12.014
  • Peer Reviewed
• [Journal Article] C_<8p>^3-C_<sp>3^ and C_<sp>^3-H Bond Activation of 1.1-Disubstituted Cyclopentane (2012)
  • Author(s): C. Mukai
  • Journal Title: J. Am. Chem. Soc. Volume: 134 Issue: 48 Pages: 19580-19583
  • DOI: 10.1021/ja309830p
  • Peer Reviewed
• [Journal Article] First Total Synthesis of (+)-Indicanone (2012)
  • Author(s): Y. Hayashi, K. Ogawa, F. Inagaki, C. Mukai
  • Journal Title: Org. Biomol. Chem. Volume: 10 Issue: 24 Pages: 4747-4751
  • DOI: 10.1039/c2ob25500f
  • Peer Reviewed
• [Presentation] Z型配位子を有するカチオン性金錯体の開発 (2014)
  • Author(s): 稲垣冬彦,松本千明,岡田泰彦,丸山直哉,向智里
  • Organizer: 日本薬学会第134年会
  • Place of Presentation: 熊本
• [Presentation] Z型配位子を有するカチオン性金錯体の開発 (2014)
  • Author(s): 稲垣冬彦, 松本千明, 岡田泰彦, 丸山直哉, 向 智里
  • Organizer: 日本薬学会第134年会
  • Place of Presentation: 熊本大学(熊本)
• [Presentation] ロジウム触媒を用いたアレニルシクロプロパン‐アルケンの立体選択的環化付加反応の反応機構の解明 (2013)
  • Author(s): 杉窪克哉,大町蕗子,宮永雄紀,稲垣冬彦,松本千明,向智里
  • Organizer: 日本薬学会北陸支部第125回例会
  • Place of Presentation: 金沢
  • Year and Date: 2013-11-17
• [Presentation] アレンを用いたロジウム(I)触媒新規環化反応の開発 (2013)
  • Author(s): 稲垣冬彦
  • Organizer: 日本薬学会北海道支部第1回薬学の有機化学を考える会
  • Place of Presentation: 北海道
  • Year and Date: 2013-07-20
• [Presentation] A New Progress in Carbonylative [2+2+1] Cycloaddition : First Utilization of Nitrile Group asπ-component (2013)
  • Author(s): T. Iwata, F. Inagaki, C. Mukai
  • Organizer: 10th International Symposium on Carbanion Chemistry
  • Place of Presentation: 京都
• [Presentation] C_<sp3>-C_<sp3> and C_<sp3>-H bond activation of 1,1-disubstituted cyclopentane (2013)
  • Author(s): C. Mukai, Y. Ohta, Y. Oura, Y. Kawaguchi, F. Inagaki
  • Organizer: 14^<th> Tetrahedron Symposium
  • Place of Presentation: Wien, Austria
• [Presentation] Total syntheses of (±)-fawcettimine, (±)-fawcettidine, (±)-lycoflexine and (±)-lycoposerramine-Q (2013)
  • Author(s): N. Itoh, Y. Hayashi, T. Iwata, H. Sugihara, F. Inagaki, C. Mukai
  • Organizer: 14^<th> Tetrahedron Symposium
  • Place of Presentation: Wien, Austria
• [Presentation] C_<sp3>- C_<sp3>活性化法の開発 (2013)
  • Author(s): 向智里,太田有羽,大浦裕貴,河口康晃,稲垣冬彦
  • Organizer: 日本薬学会第133年会
  • Place of Presentation: 横浜
• [Presentation] 連続的分子内Nicholas型反応による新規スピロアセタール骨格構築法の開発 (2013)
  • Author(s): 向智里,小嶋崇弘,川村行正,稲垣冬彦
  • Organizer: 日本薬学会第133年会
  • Place of Presentation: 横浜
• [Presentation] A New Progress in Carbonylative [2+2+1] Cycloaddition: First Utilization of Nitrile Group as π-component (2013)
  • Author(s): T. Iwata, F. Inagaki, C. Mukai
  • Organizer: 10th International Symposium on Carbanion Chemistry
  • Place of Presentation: 同志社大学(京都)
• [Presentation] Total syntheses of (±)-fawcettimine, (±)-fawcettidine, (±)-lycoflexine and (±)-lycoposerramine-Q (2013)
  • Author(s): N. Itoh, Y. Hayashi, T. Iwata, H. Sugihara, F. Inagaki, C. Mukai
  • Organizer: 14th Tetrahedron Symposium
  • Place of Presentation: Wien, Austria
• [Presentation] Csp3-Csp3 and Csp3-H bond activation of 1,1-disubstituted cyclopentane (2013)
  • Author(s): C. Mukai, Y. Ohta, Y. Oura, Y. Kawaguchi, F. Inagaki
  • Organizer: 14th Tetrahedron Symposium
  • Place of Presentation: Wien, Austria
• [Presentation] Csp3- Csp3活性化法の開発 (2013)
  • Author(s): 太田有羽
  • Organizer: 日本薬学会第133年会
  • Place of Presentation: パシフィコ横浜(神奈川県)
• [Presentation] 連続的分子内Nicholas型反応による新規スピロアセタール骨格構築法の開発 (2013)
  • Author(s): 稲垣冬彦
  • Organizer: 日本薬学会第133年会
  • Place of Presentation: パシフィコ横浜(神奈川県)
• [Presentation] アルキン-コバルト錯体及びシクロプロパンを活用した新規スピロ環構築法の開発 (2012)
  • Author(s): 向智里,小嶋崇弘,川村行正,稲垣冬彦
  • Organizer: 日本薬学会北陸支部第124回例会
  • Place of Presentation: 富山
  • Year and Date: 2012-11-18
• [Presentation] Rh(I)-Catalyzed Carbonylative [2+2+1] Cycloaddition of Bis(allene)s Toward The Synthesis of 5-8-6 Ring System (2012)
  • Author(s): S. Soraya, F. Inagaki, T. Kawamura, C. Mukai
  • Organizer: 日本薬学会北陸支部第124回例会
  • Place of Presentation: 富山
  • Year and Date: 2012-11-18
• [Presentation] アレン-ニトロンの位置選択的分子内[3+2]環化付加反応 (2012)
  • Author(s): 稲垣冬彦,小林春美,向智里
  • Organizer: 日本薬学会北陸支部第124回例会
  • Place of Presentation: 富山
  • Year and Date: 2012-11-18
• [Presentation] The Twelfth International Kyoto Conference on New Aspects of Organic Chemistry (2012)
  • Author(s): Y. Oura, Y. Ohta, Y. Kawaguchi, F. Inagaki, C. Mukai
  • Organizer: The Twelfth International Kyoto Conference on New Aspects of Organic Chemistry
  • Place of Presentation: 京都
• [Presentation] ロジウム(I)触媒を用いたエン-アレニルシクロプロパンの高立体選択的新規環化反応 (2012)
  • Author(s): 向智里,杉窪克哉,宮永雄紀,大町蕗子,松本千明,稲垣冬彦
  • Organizer: 第38回反応と合成の進歩シンポジウム-ライフサイエンスを志向した理論、反応および合成-
  • Place of Presentation: 東京
• [Presentation] ニトリルを反応成分とするPauson-Khand反応の開発 (2012)
  • Author(s): 向智里,岩田隆,中野高幹,稲垣冬彦
  • Organizer: 第42回複素環化学討論会
  • Place of Presentation: 京都
• [Presentation] Rh(I)-Catalyzed [7+2] Cycloaddition via C-C Bond Activation of Cyclopentane (2012)
  • Author(s): F. Inagaki
  • Organizer: The Twelfth International Kyoto Conference on New Aspects of Organic Chemistry
  • Place of Presentation: リーガロイヤルホテル(京都府)
• [Presentation] ロジウム(I)触媒を用いたエン-アレニルシクロプロパンの高立体選択的新規環化反応 (2012)
  • Author(s): 稲垣冬彦
  • Organizer: 第38回反応と合成の進歩シンポジウム
  • Place of Presentation: タワーホール船堀(東京都)
• [Presentation] ニトリルを反応成分とするPauson-Khand反応の開発 (2012)
  • Author(s): 岩田 隆
  • Organizer: 第42回複素環化学討論会
  • Place of Presentation: 京都テルサ(京都府)
• [Presentation] ロジウム触媒を用いたアレニルシクロプロパン‐アルケンの立体選択的環化付加反応の反応機構の解明
  • Author(s): 杉窪克哉，大町蕗子，宮永雄紀，稲垣冬彦，松本千明, 向 智里
  • Organizer: 日本薬学会北陸支部第125回例会
  • Place of Presentation: 北陸大学(金沢)
• [Presentation] アレンを用いたロジウム(I)触媒新規環化反応の開発
  • Author(s): 稲垣 冬彦
  • Organizer: 日本薬学会北海道支部 第１回薬学の有機化学を考える会
  • Place of Presentation: 北海道大学(札幌)
  • Invited
• [Presentation] アルキン-コバルト錯体及びシクロプロパンを活用した新規スピロ環構築法の開発
  • Author(s): 小嶋崇弘
  • Organizer: 日本薬学会北陸支部第124回例会
  • Place of Presentation: 富山大学(富山県)
• [Presentation] Rh(I)-Catalyzed Carbonylative [2+2+1] Cycloaddition of Bis(allene)s Toward The Synthesis of 5-8-6 Ring System
  • Author(s): S. Soraya
  • Organizer: 日本薬学会北陸支部第124回例会
  • Place of Presentation: 富山大学(富山県)
• [Presentation] アレン-ニトロンの位置選択的分子内[3+2]環化付加反応
  • Author(s): 稲垣冬彦
  • Organizer: 日本薬学会北陸支部第124回例会
  • Place of Presentation: 富山大学(富山県)