Asymmetric Synthesis of the Biologically Active Compounds by the Diastereoselective Acetal Formation Reaction
| Project/Area Number |
21590001
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Musashino University (2011)
Tohoku University (2009-2010) |
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Principal Investigator |
HIROYA Kou 武蔵野大学, 薬学研究所, 教授 (70192721)
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| Project Period (FY) |
2009 – 2011
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| Project Status |
Completed (Fiscal Year 2011)
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| Budget Amount *help |
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2010: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2009: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
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| Keywords | 有機化学 / 非対称化反応 / 生理活性化合物 / 不斉合成 / 不斉第四級炭素 / アセタール化反応 / 分子内水素結合 / 環化反応 / 不斉全合成 / cepharamine / Lycopladine A |
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| Research Abstract |
The hydroxyl group on the side chain at C2-position of 1, 3-cyclohexanedione derivatives discriminates carbonyl group on the ring to produce the hemiketal stereoselectively depending on its absolute configuration. The intramolecular ketals were afforded as almost single compound from the hemiketals. When the hemiketals were converted to the intermolecular ketals, the other ketone was selected. Namely, the optically active compounds, which contain the different absolute configuration at the quaternary carbon center, could be synthesized from the single molecule. Although the hydrogen bonding plays the important role for the diastereoselective hemiketal formation reaction, it was also clarified that the steric demand is more important for the different kind of substrates. The asymmetric synthesis of BCD ring system of (+)-cepharamine and (+)-lycopladine A were also accomplished utilizing the diastereoselective hemiketal formation reactions as a key step.
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Report
(4 results)
Research Products
(63 results)
