Synthesis of 1,3-Dipoles from Amides
| Project/Area Number |
18K05127
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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 |
Sato Takaaki 慶應義塾大学, 理工学部(矢上), 准教授 (70509926)
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| Project Period (FY) |
2018-04-01 – 2021-03-31
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| Project Status |
Completed (Fiscal Year 2020)
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| Budget Amount *help |
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2020: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
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| Keywords | 有機合成化学 / 天然物化学 / アミド基 / 求核付加反応 / 1,3-双極子 / アミド / ニトロン / アゾメチンイリド / 天然物の全合成 ３．研究課題名 / 天然物の全合成 / 有機化学 |
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| Outline of Final Research Achievements |
1,3-Dipoles have been widely used as promising intermediates for the synthesis of complex heterocyclic compounds found in biologically active natural products and pharmaceuticals. Therefore, the development of practical methods to generate highly functionalized 1,3-dipoles is an important research topic in the modern organic synthesis. Our research group has proposed that easily available amides can serve as synthetic equivalents of 1,3-dipoles through reduction or nucleophilic addition. In this project, we developed Ir-catalyzed reduction or nucleophilic addition to N-hydroxyamides. The method provided functionalized nitrones, and was successfully applicable to the total synthesis of cylindricine C. The iridium-catalyzed reduction was also applied to the synthesis of functionalized azomethine ylides, which resulted in the total synthesis of aspidospermidine.
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| Academic Significance and Societal Importance of the Research Achievements |
本研究では、「安定で官能基変換の難しいアミド基を自在に操れるか」という有機合成化学上の難問に挑戦した。アミド基への求核付加反応は、多官能基化された含窒素化合物を即座に与えるため、天然物合成・創薬合成を指向した複雑な分子の革新的反応となる可能性を秘めている。しかし、アミド基への求核付加反応は、アミド基自体の高い安定性のために開発が難しく、長年見過ごされてきた。本研究において、環状ニトロンの精密合成を可能とし、複雑な多環性構造を有する生物活性化合物の実用的な供給法が開発された。また、本ニトロン合成法は、アゾメチンイリドなど、様々な1,3-双極子の合成へと展開し、一般性の高い方法論へと拡張できた。
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Report
(4 results)
Research Products
(51 results)
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[Journal Article] Unified Total Synthesis of Madangamine Alkaloids2019
Author(s)
Suto, T.; Yanagita, Y.; Nagashima, Y.; Takikawa, S.; Kurosu, Y.; Matsuo, N.; Miura, K.; Simizu, S.; *Sato, T.; *Chida, N.
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Journal Title
Bulletin of the Chemical Society of Japan
Volume: 92
Issue: 3
Pages: 545-571
DOI
NAID
Related Report
Peer Reviewed
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