Studies on the syntheses of berkeleydione family natural products through a construction of the bridged polycyclic system by a polycyclization reaction
| Project/Area Number |
26460011
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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 |
Chemical pharmacy
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| Research Institution | Nagoya City University |
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Principal Investigator |
NAKAMURA Seiichi 名古屋市立大学, 大学院薬学研究科, 教授 (90261320)
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | バークレーオン類 / メロテルペノイド / 抗腫瘍性 / 架橋多環式骨格 / ポリエン環化反応 / 協奏反応 / 立体選択的 / 閉環メタセシス反応 / エポキシアリルシラン / 閉環メタセシス / 塩化鉄 / 非対称化 / キラル塩基 / 不斉脱プロトン化 / 抗腫瘍活性 / バークレージオン類 / いす形－いす形遷移状態 / プロトオースチノイドA |
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| Outline of Final Research Achievements |
Toward total syntheses of bioactive meroterpenoids berkeleyones, a stereoselective method for the construction of bridged polycyclic systems by a biomimetic polycyclization reaction has been developed. A model study revealed that the desired reaction proceeded in a concerted manner upon treatment of epoxyallylsilanes with diethylaluminum chloride, leading to the regio- and stereoselective formation of bridged polycyclic compounds. The cyclization product having an oxygen functionality at C8 was successfully converted to C3-dehydrated berkeleytrione through a ring-closing metathesis reaction.
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Report
(4 results)
Research Products
(10 results)
