| Project/Area Number |
05453186
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
医薬分子機能学
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| Research Institution | Kumamoto University |
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Principal Investigator |
KUNIEDA Takehisa Kumamoto University, Pharmceutical Sciences ; Professor, 薬学部, 教授 (80012649)
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| Co-Investigator(Kenkyū-buntansha) |
ISHIZUKA Tadao Kumamoto University, Pharmaceutical Sciences ; Assistant, 薬学部, 助手 (60176203)
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| Project Period (FY) |
1993 – 1994
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| Project Status |
Completed (Fiscal Year 1994)
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| Budget Amount *help |
¥7,300,000 (Direct Cost: ¥7,300,000)
Fiscal Year 1994: ¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 1993: ¥3,800,000 (Direct Cost: ¥3,800,000)
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| Keywords | 2-Amino alcohol / 2-Oxazolone / 2-Oxazolidinone / Asymmetric synthesis / Chiral auxiliary / Hydroxy amino acid / Asymmetric reduction / Chiral Synthesis / アルドール反応 |
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| Research Abstract |
1.Development of Novel Chiral Synthons for Unusual Amino Acids
Intramolecular radical cyclizations of 2,2-dichloroacyl groups to the olefinic moiety of 2-oxazolone followed by dechlorination with (Me_3) _3SiH furnished an excellent route for the stereoselective preparation of 2-aminoalcohol chiral synthons with three ajacent asymmetric centers.
2.Chiral Synthesis of Hydroxyamino Acids of Biological Significance
Diastereoselective aldol reactions between alpha-amino aldehydes and N-acetyl derivatives of the chiral 2-oxazolidinones previously developed as chiral auxiliaries resultedin stereoselective formation of gamma-amino-beta-hydroxy acids which served as the compornents essential for the renin inhibitory peptides.
3.Higly Efficient Catalytic Reductions of Ketones
Asymmetric reduction of ketones with BH_3 proceeded with catalytic amount of the 2-aminoalcohol derived from the newly developed 2-oxazolidinone, HMCOx, to give the enantiomerically pure secondary alcohols.
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