| Project/Area Number |
16K13085
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Biomolecular chemistry
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| Research Institution | Waseda University |
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Principal Investigator |
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| Project Period (FY) |
2016-04-01 – 2018-03-31
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| Project Status |
Completed (Fiscal Year 2017)
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| Budget Amount *help |
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | フシコクシン / 全合成 / 環変換反応 / 天然物合成 / シクロプロパン化 / Buchner反応 / ロジウム触媒 / ジアゾカルボニル化合物 / 誘導体合成 / 植物生長制御分子 / 構造活性相関研究 / 環拡大反応 |
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| Outline of Final Research Achievements |
We tried to synthesize tricyclic carbon skeleton aiming at the total synthesis of natural product, fusicoccin A Introduction of a side chain of 4 carbon units into benzene and conversion of 4-6-4 carbon skeleton into 5-8-5 condensed ring structure was an extremely novel synthesis plan. That is, it performs continuous ring extension reaction from substituted benzene and converts the 6-membered ring to 8-membered ring. A Buchner reaction was attempted by reacting a substituted benzene obtained in 7 steps from a commercially available compound with a Rh (II) catalyst. As a result, stereoselective cyclopropanation conditions were found and the subsequent 7-membered ring was quantitatively obtained with nearly a single product by divinylcyclopropane rearrangement of the intermediate.
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| Academic Significance and Societal Importance of the Research Achievements |
生物活性をもつ天然有機化合物などの主骨格を直感的かつ効率的に構築する方法の開発は医農薬の開発段階で利用され、ひいては画期的な製品導出の一助となる。本研究はベンゼンに4炭素ユニットの側鎖を導入し、4-6-4炭素骨格を5-8-5縮環構造に変換するという極めて斬新な合成計画であり、これが一般化されば、創薬現場での利用が期待できる。今回、すべての骨格を合成することはできなかったが、立体選択的に５－７員環を構築する手法を開発することができた。
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