| Project/Area Number |
15K05420
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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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| Research Field |
Organic chemistry
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| Research Institution | Shinshu University |
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Principal Investigator |
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| Project Period (FY) |
2015-04-01 – 2018-03-31
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| Project Status |
Completed (Fiscal Year 2017)
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| Budget Amount *help |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
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| Keywords | シクロプロパン / 不斉合成 / リグナン / 天然物 / 炭素炭素結合切断 / 開環 / 環化 / 生物活性物質 / オキシホモマイケル反応 / 1,5-付加 / 全合成 / 銅触媒 / 構造訂正 / 環開裂 / 高立体選択的 / エナンチオマー / ジアステレオマー / ラクトン / 生物活性 |
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| Outline of Final Research Achievements |
We investigated ring-opening cyclization, homo-Nazarov cyclization, oxy-homo-Michael reaction, 1,5-addition and reductive ring-opening reaction of enantioenriched donor-acceptor cyclopropanes. In addition, a couple of asymmetric total synthesis of bioactive lignans using a couple of these reactions as key steps. Namely, we achieved the asymmetric total synthesis of tupichilignan A using the highly stereoselective Cu-catalyzed oxy-homo-Michael (OHM) addition of alcohols into bicyclic donor-acceptor cyclopropanes as a key step. Moreover, Cu-catalyzed 1,5-addtion of Grignard reagent instead of alcohols into the enantioenriched donor-acceptor cyclopropanes also proceeded with high regio- and stereoselectivity. In addition, we reported the reductive ring-opening of D-A cyclopropanes and its application for the total synthesis of yatein. Beside the intermolecular reaction, we verify the reaction mechanism of ring-opening cyclization and homo-Nazarov cyclization of D-A cyclopropanes.
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