Development of the efficient synthetic methods of multi-cyclic biologically active natural products
| Project/Area Number |
18H01984
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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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 |
CHIDA Noritaka 慶應義塾大学, 理工学部(矢上), 教授 (50197612)
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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 |
¥15,860,000 (Direct Cost: ¥12,200,000、Indirect Cost: ¥3,660,000)
Fiscal Year 2020: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2019: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2018: ¥8,580,000 (Direct Cost: ¥6,600,000、Indirect Cost: ¥1,980,000)
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| Keywords | タキソール / ネオツベロステモニン / 化学合成 / サマリウム環化 / 多環性構造 / タキソール合成 / ネオツベロステニン |
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| Outline of Final Research Achievements |
In this project, to establish the synthetic way to structurally complex natural products possessing multi-cyclic system, total syntheses of taxol and neotuberostemonine were investigated. On the synthetic study of taxol, total synthesis was achieved utilizing the Sm-mediated construction of eight-membered ring and the introduction of bridge-head olefin by the double Rubottom oxidation as the key transformation. On the other hand, the total synthesis of neotuberostemonine was also accomplished. The sequential sigmatropic rearrangements, Sm-mediated cyclization and lactam-selective nucleophilic addition were employed for the synthesis. These achievements established the stereoselective chiral synthesis of structurally complex multi-cyclic natural products.
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| Academic Significance and Societal Importance of the Research Achievements |
有用な生物活性を有する天然有機化合物には，複雑な多環性構造を有するものが多いが，これら多環性構造を効率的に化学合成ことは必ずしも容易ではない。本研究においては，タキソール，ネオツベロステモニンという多環性天然物の全合成を行うことにより，新規な多環性構造構築法開発に取り組んだ。その結果タキソールおよびネオツベロステモニンをともに全合成することができた。この成果は合成が難しいとされていた複雑な構造を有する天然有機化合物の新規合成法を示したもので，学術的意義は大きい。またタキソールのような抗ガン剤として用いられている化合物の安定的な供給にも資するものであるり，社会的意義も意義も小さくない。
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Report
(4 results)
Research Products
(65 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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