Synthetic studies of indolenine derivative with an asymmetric quaternary carbon

2009 Fiscal Year Final Research Report

• Project/Area Number: 20890129
• Research Category: Grant-in-Aid for Young Scientists (Start-up)
• Allocation Type: Single-year Grants
• Research Field: Drug development chemistry
• Research Institution: Nara Institute of Science and Technology
• Principal Investigator: KAGAWA Natsuko Nara Institute of Science and Technology, 大学院・薬学研究院, 助教 (60467686)
• Project Period (FY): 2008 – 2009
• Keywords: インドール / インドレニン / 互変異性体 / 立体選択性 / パラジウム / マグネシウム / ヨヒンビン / レゼルピン

Research Abstract

Medicinal components in reserpine (hypotensive drugs & tranquilizers) and ajmaline (antiarrhythmic drugs) have a common chemical structure "indole", however possess different biological activities. An indole core in the reserpine was changed into an indolenine core by organic synthetic chemistry in order to clear a chemical role of indole. The molecular structure of indolenine was identified and characterized with scientific evidence.

Research Products

• [Journal Article] Rare earth triflates/chlorotrimethylsilane induced activation of triethylamine as a latent acetaldehyde anion : a new synthesis of α,β-unsaturated aldehydes (2010)
  • Author(s): Natsuko Kagawa, Yoshiko Sasaki, Hideo Kojima, Masahiro Toyota
  • Journal Title: Tetrahedron Letters Vol.51, No.3 Pages: 482-484
  • Peer Reviewed
• [Journal Article] Rh(I)-Catalyzed CO Gas-Free Carbonylative Cyclization Reactions of Alkynes with 2-Bromophenylboronic Acids Using Formaldehyde (2009)
  • Author(s): Tsumoru Morimoto, Kae Yamasaki, Akihisa Hirano, Ken Tsutsumi, Natsuko Kagawa, Kiyomi Kakiuchi, Yasuyuki Harada, Yoshiya Fukumoto, Naoto Chatani, Takanori Nishioka
  • Journal Title: Organic Letters Vol.11, No.8 Pages: 1777-1780
  • Peer Reviewed
• [Presentation] グアニジン触媒を用いた2,2-ジ置換キラルクロマン化合物の不斉合成研究 (2010)
  • Author(s): 徳能紗也香, 中西和嘉, 熊本卓哉, 加川夏子, 石川勉
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
  • Year and Date: 2010-03-28
• [Presentation] 3-アリールアジリジン-2-カルボキシレートを利用したポドフィロトキシンの合成研究 (2010)
  • Author(s): 高橋正人, 加川夏子, 熊本卓哉, 石川勉
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
  • Year and Date: 2010-03-28
• [Presentation] インドールのC3位選択的なアリル化反応におけるインドレニン成績体の安定性と立体選択性の発生メカニズムについて (2010)
  • Author(s): 加川夏子
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 東大阪 (大阪)
  • Year and Date: 2010-03-26
• [Presentation] グアニジン触媒を用いた2,2-ジ置換キラルクロマン化合物の不斉合成研究 (2009)
  • Author(s): 徳能紗也香, 中西和嘉, 熊本卓哉, 加川夏子, 石川勉
  • 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: 2009-11-16
• [Presentation] ミロエステロール合成に向けたドミノ環化を利用した鍵中間体の合成研究 (2009)
  • Author(s): 秋元麻友子, 熊本卓哉, 加川夏子, 石川勉
  • Organizer: 第53回香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 生駒 (奈良)
  • Year and Date: 2009-11-08
• [Presentation] The Synthetic Study of C3-Branched Indole : As an Approach to the Formation of Chiral Indolenine (2008)
  • Author(s): Ade Arsianti, Natsuko Kagawa, Tsumoru Morimoto, Kiyomi Kakiuchi
  • Organizer: The 8^<th> GIST/NAIST Joint Symposium on Advanced Materials
  • Place of Presentation: 生駒 (奈良)
  • Year and Date: 2008-11-26
• [Presentation] 立体障害性インドールに対するパラジウム触媒を用いたβ-アリル化によるインドレニン類の合成 (2008)
  • Author(s): 加川夏子, Jeremiah P. Malerich, Ye Zhu, Viresh H. Rawal
  • Organizer: 第38回複素環化学討論会
  • Place of Presentation: 福山 (広島)
  • Year and Date: 2008-11-21
• [Presentation] New Development and Requirement of Indole Chemistry-Syntheses of Indolenine Derivative (2008)
  • Author(s): Natsuko Kagawa, Jeremiah P. Malerich, Ye Zhu, Viresh H. Rawal
  • Organizer: 18^<th> International Symposium on Fine Chemistry and Functional Polymers (FCFP-XVIII) & IUPAC 4^<th> International Symposium on Novel Materials and Synthesis (NMS-IV)
  • Place of Presentation: Zhenjiang (China)
  • Year and Date: 2008-10-16