Construction of Bicyclo[3.2.1]octene Derivertives via [4+1] Cycloaddition Reaction
| Project/Area Number |
19K06968
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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 47010:Pharmaceutical chemistry and drug development sciences-related
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| Research Institution | Tohoku University |
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Principal Investigator |
Kato Nobuki 東北大学, 理学研究科, 講師 (50400221)
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| Project Period (FY) |
2019-04-01 – 2022-03-31
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| Project Status |
Completed (Fiscal Year 2021)
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| Budget Amount *help |
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2021: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2020: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2019: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
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| Keywords | 有機合成 / [4+1]環化付加反応 / ジメトキシカルベン / bicyclo[3.2.1]octane / 始原植物ホルモン |
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| Outline of Research at the Start |
本研究は、ジメトキシカルベンと環状ジエンの[4+1]環化付加反応を用いた架橋型二環式骨格bicyclo[3.2.1]octaneおよびbicyclo[2.1.1]hexaneの1段階構築法を開発し、これらの低分子医薬品への展開の際に妨げとなっている合成の煩雑さを解消することを目的とする。さらに、本反応の有用性の向上と実証を目的として、本反応の不斉反応化ならびに生理活性天然物の全合成への応用へと研究を展開する。
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| Outline of Final Research Achievements |
We developed a new one-step construction of bicyclo[3.2.1]octane skeleton by intermolecular [4+1] cycloaddition of dimethoxycarbenes and cyclic dienes, and found that the reactivity is dramatically improved by introducing strong electron-withdrawing groups to the diene. Additionally, we also accomplished the synthesis of the ancient phytohormones dn-cis-OPDA and dn-iso-OPDA, the ancestors of the plant hormone isoleucine jasmonate, and their analogs dn-cis-OPDA-Ile and dn-iso-OPDA-Ile, cis-OPDA-Ile, iso-OPDA- Ile and iso-OPDA-Ile. adducts.
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| Academic Significance and Societal Importance of the Research Achievements |
架橋型二環式骨格bicyclo[3.2.1]octaneは、低分子創薬において芳香環に代わる次世代の基本骨格のひとつとして期待されている。本研究では、ジメトキシカルベンとジエンの分子間[4+1]環化付加反応に着目し、従前の合成法ではなし得なかったbicyclo[3.2.1]octaneの1段階構築を実現した点で意義深い。また、始原植物ホルモンdn-cis-OPDA、dn-iso-OPDAおよびその類縁体の合成にも成功、これらを用いた植物ホルモンの生物学的研究が進行しており、植物ホルモン進化の詳細解明が期待される。
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Report
(4 results)
Research Products
(42 results)
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[Journal Article] Deciphering OPDA signaling components in the momilactone-producing moss Calohypnum plumiforme2021
Author(s)
Hideo Inagaki, Koji Miyamoto, Noriko Ando, Kohei Murakami, Koki Sugisawa, Shion Morita, Emi Yumoto, Miyu Teruya, Kenichi Uchida, Nobuki Kato, Takuya Kaji, Yousuke Takaoka, Yuko Hojo, Tomonori Shinya, Ivan Galis, Akira Nozawa, Tatsuya Sawasaki, Hideaki Nojiri, Minoru Ueda, Kazunori Okada
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Journal Title
Frontiers in Plant Science
Volume: -
Pages: 688565-688565
DOI
Related Report
Peer Reviewed / Open Access
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[Presentation] Chemical tuning of target selectivity by using stereochemical library of a natural product coronatine2021
Author(s)
Kengo Hayashi, Nobuki Kato, Raku Watanabe, Yousuke Takaoka, Haruna Nomoto, Misuzu Nakayama, Saki Miyagawa, Koji Miyamoto, Hideo Inagaki, Kazunori Okada, Takuya Kaji, Minoru Ueda
Organizer
Pacifichem2021
Related Report
Int'l Joint Research
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