2022 Fiscal Year Final Research Report
Development of new organocatalyst with 1,3-diarylpropane structure and its application toward asymmetric synthesis of polycyclic indoles
| Project/Area Number |
20K05502
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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| Research Institution | Kobe Pharmaceutical University (2022)
Kanagawa University (2020-2021) |
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Principal Investigator |
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| Project Period (FY) |
2020-04-01 – 2023-03-31
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| Keywords | cascade reaction / organocatalyst / 2-pyridone / Passerini reaction / polycyclic indole |
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| Outline of Final Research Achievements |
The interrupted Passerini reaction of 3-(2-isocyanoethyl)-indole catalyzed by 3,5,6-trifluoro-2-pyridone was developed. The reaction diastereoselectively provided a tetracyclic furoindoline, which proved to be a good substrate for further transformations. Therefore, the sequential reactions, such as interrupted Passerini/Joullie-Ugi reaction were performed in one-pot to rapidly provide versatile and highly functionalized indolines from 3-(2-isocyanoethyl)-indole.
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| Free Research Field |
有機合成化学
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| Academic Significance and Societal Importance of the Research Achievements |
多成分連結反応やカスケード反応は、単純な分子から複雑な機能性分子を迅速に合成でき、近年注目を浴びている分野の一つである。今回、これまでに注目されてこなかった2-ピリドンの性質に目を付け、2-ピリドンを触媒に用いた連続反応、及び、その不斉触媒化に取り組んだ。その結果、トリプタミン由来のイソシアニドから、1-potで高度に官能基化された様々なインドリンへ導くことができた。本手法を用いることにより、様々な生物活性天然物の合成や生物活性が期待される天然物様化合物の迅速な合成が期待される。
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