| Project/Area Number |
22790017
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kitasato University |
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Principal Investigator |
HIROSE Tomoyasu 北里大学, 大学院・感染制御科学府, 准教授 (00370156)
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| Project Period (FY) |
2010 – 2011
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| Project Status |
Completed (Fiscal Year 2011)
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| Budget Amount *help |
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2011: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
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| Keywords | 有機化学 / 天然物 / 抗マラリア活性 / アパリシン類 / ヒドロキシアパリシン / インドールアルカロイド / ワンポットカスケード反応 / 擬アミナール / 不斉全合成 |
|---|
| Research Abstract |
Hydroxyapparicine was isolated from Tabernaemontana dichotoma in 1984.Then, the relative stereochemistry was proposed that recorded spectral data. However, C15 stereochemistry was not showed. Therefore, absolute stereochemistry of Hydroxyapparicine has never determined. Structure fearture of hydroxyapparicine is 1-azabicyclo[4.2.2] decane and C16 chiral tertiary alchol moiety connected indole 2-position. Moreover, tertiary alchol moiety is unstable under acidic conditions. It was easliy dedydration of similar compound. From synthetic standpiont, synthesis of pseudo-aminal type alkaloids need to novel method under mild conditions. Herein, we repored the stereoselective total synthsis and determination of absolute stereochemistry of 16R-hydroxy-16, 22-dihydroapparicine(Hydroxyapparicine).
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