Nucleophilic Additions to Cyclic N-Acyliminium Ions: Inverse Stereoselectivity
Project/Area Number |
16K05777
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Multi-year Fund |
Section | 一般 |
Research Field |
Synthetic chemistry
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Research Institution | Okayama University |
Principal Investigator |
Suga Seiji 岡山大学, 自然科学研究科, 教授 (50291430)
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Project Period (FY) |
2016-04-01 – 2019-03-31
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Project Status |
Completed (Fiscal Year 2018)
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Budget Amount *help |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2018: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
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Keywords | イミニウムイオン / 立体化学 / 求核剤 / カチオンプール法 / イミニウムカチオン |
Outline of Final Research Achievements |
Cyclic alkaloids often have high biological activity, and development of their stereoselective synthesis is one of the most important issues in this research area. In this study, the stereochemistry in the reaction of the N-acyliminium ion intermediates generated by the indirect cation pool method was investigated. As a result of research focusing on the inverse stereochemistry phenomena, we show the generality of this phenomenon. In addition, some control experiments were conducted for the elucidation of mechanism of this phenomenon, and applications were also examined.
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Academic Significance and Societal Importance of the Research Achievements |
不安定な反応中間体である環状の有機カチオンの立体化学に関する知見は、非常に乏しく、これを分光学的に決定し、選択性を論じる試みはほとんどなかった。本研究はインダイレクトカチオンプール法を用いてこれらの反応の立体化学を基礎的な部分から再度見直し、検証することで、有機合成において極めて重要なN-アシルイミニウムイオンの化学全体を俯瞰しようとする研究であり、有機カチオン化学と医薬品に多くみられる環状アルカロイド合成の分野においてその意義は極めて大きい。
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Report
(4 results)
Research Products
(69 results)
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[Journal Article] Synthetic Terrein Inhibits Progression of Head and Neck Cancer by Suppressing Angiogenin Production2016
Author(s)
Akane Shibata, Soichiro Ibaragi, Hiroki Mandai, Toki Tsumura, Koji Kishimoto, Tatsuo Okui, Nur Mohammad Monsur Hassan, Tsuyoshi Shimo, Kazuhiro Omori, Guo-Fu Hu, Shogo Takashiba, Seiji Suga, and Akira Sasaki
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Journal Title
Anticancer Res.
Volume: 36
Pages: 2161-2168
Related Report
Peer Reviewed / Int'l Joint Research
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