| Project/Area Number |
23590035
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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 | Tokushima Bunri University |
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Principal Investigator |
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| Project Period (FY) |
2011 – 2013
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| Project Status |
Completed (Fiscal Year 2013)
|
| Budget Amount *help |
¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2013: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2011: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
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| Keywords | tetraalkylated center / all-carbon center / asymmetric reaction / 1,4-addititon / alkylation / dihydroxyanonene / organic synthesis / quaternary / 不斉1,4-付加反応 / テトラアルキル不斉4級炭素 / 不斉アルドール反応 / bakuchiol, (+)- / 全合成 / 脱オキサゾリジノン / 脱炭酸 / テトラアルキル四級炭素 / オールカーボン四級炭素 / 不斉合成 / 不斉α-アルキル化 / 不斉アルドール / 連続不斉中心 / 天然物合成 / 不斉1,4-付加 / 不斉アルキル化 / テトラアルキル炭素 |
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| Research Abstract |
Diihydroxyanones attract many researchers as lead compounds for the development of anti-Alzheimer's disease or the learning improvement drugs due to the increasing effect to the activity of neurotrophins. In this study, we achieved the construction of tetraalkyl chiral quaternary carbon center utilizing diastereoselective 1,4-addition of divinylcuplate to the unsaturated carboxylic acid consisting chiral oxazolidinone as a chiral auxiliary in high diastereoselectivity. Subsequently, the 1,4-adduct was reacted with iodomethane after the treated with SHMDS, converted to alfa-alkylated compound with high diastereoselectivity. These reactions allowed to induce chiralities at C8,9 of dihydroxyanones. The removal of oxazolidinone was hard. The usual basic condition, hydroxyperoxide with alkaline or reduction did not proceed. Eventually, we found that LiAlH4 reduction after the substitution with sodium ethylthiolate give the corresponding alcohol in high yield.
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