2022 Fiscal Year Final Research Report
Development and application of oxidative coupling between arenes and alkenes
| Project/Area Number |
20K05499
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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 | Keio University |
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Principal Investigator |
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| Project Period (FY) |
2020-04-01 – 2023-03-31
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| Keywords | フェノール / アルケン / 酸化 / 炭素ー炭素結合形成 / 環化 / テルペノイド / テトラペタロン |
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| Outline of Final Research Achievements |
We succeeded in developing the construction method of bicyclic skeletons by oxidative aromatic nucleophilic substitution on phenols with alkenyl side chains using hypervalent iodine oxidation reagent. Various aliphatic bicyclic compounds and heterocycles were synthesized from substrates with various alkenyl side chains, electron-donating/withdrawing substituents, and heteroatoms. The developed method was applied to the synthesis of 6/5-membered bicyclic core of tetrapetalone A. This method is useful for syntheses of various bioactive compounds and medicines.
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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 |
炭素－炭素結合形成反応は、医薬品や生物活性有用物質、機能性物質の合成において、その骨格を構築する中心的な化学反応であり、その新しい方法論の開発は、これら化合物の効率的合成、新しい物質創製、機能性の創出を実現する重要な研究課題である。本課題で開発した酸化的芳香族－アルケンカップリングによる炭素－炭素結合形成反応は、医薬品や生物活性物質に含まれるさまざまな脂肪族、複素環の二環性化合物の合成に有用で、これらの供給と創製に大きく貢献する。
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