2003 Fiscal Year Final Research Report Summary
Creation of Asymmetric Catalysts Based on New Concept, and Their Application to Efficient Synthesis of Pharmaceutical Lead Compounds
| Project/Area Number |
13307062
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| Research Category |
Grant-in-Aid for Scientific Research (A)
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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 | The University of Tokyo |
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Principal Investigator |
KANAI Motomu The University of Tokyo, Graduate School of Pharmaceutical Sciences, Associate Professor, 大学院・薬学系研究科, 助教授 (20243264)
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| Co-Investigator(Kenkyū-buntansha) |
MATSUNAGA Shigeki The University of Tokyo, Graduate School of Pharmaceutical Sciences, Research Associate, 大学院・薬学系研究科, 助手 (50334339)
OHSHIMA Takashi The University of Tokyo, Graduate School of Pharmaceutical Sciences, Research, 大学院・薬学系研究科, 助手 (10313123)
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| Project Period (FY) |
2001 – 2003
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| Keywords | asymmetric catalyst / bifunctional catalysis / pharmaceutical lead / asymmetric synthesis / biologically active natural products / asymmetric cyanosil lation / asymmetric aldol reaction / asymmetric Mannich reaction |
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| Research Abstract |
We developed a chiral heteropolymetallic complex containing a lanthanide metal, alkali metal, and BINOL. This new catalyst promotes the direct enantioselective aldol reaction from unmodified ketones and aldehydes with high enantioselectivity. We also developed a novel chiral ligand, linked BINOL, and found that the zinc complex can promote very efficient C-C bond formation between a hydroxyl ketone and aldehydes or imines. The maximum catalyst turnover was reached up to 20000 with maintaining an excellent enantioselectivity. Moreover, we developed a new sugar-derived catalyst that can promote enantioselective cyanosilylation of ketones and ketoimines with high efficiency. Using these catalyses, we established efficient synthetic route of camptothecin (anticancer drug), oxybutynin (muscarinic receptor antagonist), and sorbinil (aldose reductase inhibitor). These synthetic route have a potential of being applied to industrial synthesis.
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