2019 Fiscal Year Final Research Report
Development of a 1,2-Metallate rearrangement of boracycles: A rapid construction of highly functionalized cyclic- and acyclic-scaffolds
| Project/Area Number |
19K21128
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| Project/Area Number (Other) |
18H05978 (2018)
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| Research Category |
Grant-in-Aid for Research Activity Start-up
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| Allocation Type | Multi-year Fund (2019)
Single-year Grants (2018) |
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| Review Section |
0501:Physical chemistry, functional solid state chemistry, organic chemistry, polymers, organic materials, biomolecular chemistry, and related fields
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| Research Institution | Okayama University |
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Principal Investigator |
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| Project Period (FY) |
2018-08-24 – 2020-03-31
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| Keywords | 有機ホウ素化合物 / 有機合成 / アート錯体 / 1,2-メタレート転位 / 立体選択的反応 |
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| Outline of Final Research Achievements |
Organoboron compounds are important class of molecules which were often used as intermediates for the synthesis of pharmaceutical and functional material. Additionally, boron containing medicines such as Bortezomib are known to possess a unique and potent activity. In this study, we aimed to develop new synthetic methodologies for the rapid synthesis of highly substituted boronic ester derivatives inspired by 1,2-metallate rearrangement of alkenylboron-ate complex. To realize this goal, we developed 1) ring-contractive metallate rearrangement of boracycle, for the synthesis of densely functionalized cyclic boronic ester derivatives, and 2) aryne-triggered multicomponent metallate rearrangement for the synthesis of liner, highly substituted boronic ester derivatives.
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| Free Research Field |
有機合成化学、天然物化学
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| Academic Significance and Societal Importance of the Research Achievements |
本研究では、医薬品や生物活性天然物の合成を容易にするための、複雑な構造（多くの置換基や官能基）を持つ有機ホウ素化合物の有機合成手法を開発した。ホウ素元素の特性となるボロン酸エステルアート錯体の1,2-メタレート転位は従来２つのビルディングブロックの連結に使われることが多かったが、本研究では環構造などの分子の骨格を組み上げながら有機ホウ素化合物を合成するための手法に展開した。ホウ素を活用する有機合成に新たな知見を与えるとともに、創薬等に応用可能な技術であると期待している。
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