2002 Fiscal Year Final Research Report Summary
Development of highly effective rhodium-catalyzed reaction and its application
| Project/Area Number |
13672243
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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 | Kyoto Pharmaceutical University |
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Principal Investigator |
IKEDA Masazumi Kyoto Pharmaceutical University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (30028857)
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| Co-Investigator(Kenkyū-buntansha) |
YAKURA Takayuki Kyoto Pharmaceutical University, Faculty of Pharmaceutical Sciences, Assistant Professor, 薬学部, 講師 (70220126)
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| Project Period (FY) |
2001 – 2002
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| Keywords | dirhodium(II) catalyst / C-H insertion reaction / chemo- and stereo-selective / α-diazoketone / cyclpentanone / 3(2H)-furanone / β-hydroxy acid / cyclization |
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| Research Abstract |
Development of novel highly chemo- and stereo-selective dirhodium(II)-catalyzed C-H insertion reaction of α-diazoketones controlled by stereo-electronic effect of tert-butyldimethosilyl group was achieved. As a result, a variety of functionalized cyclpentanones have been easily prepared. And the new acceleration method of the Baeyer-Villiger reaction of polysubstituted cyclopentanones was found to give polysubstituted δ-lactones. These new reactions applied to efficient syntheses of Corey lactone, an important intermediate of prostagrandins, and lactone portion of antitumor marine antibiotics discodermolide.
A new methodology for the asymmetric synthesis of β-hydroxy acid was developed. Dirhodium(II)-catalyzed C-H insertion of α-alkoxydiazoketone, which was prepared from primary alkyl halide and readily available chiral α-hydroxy acid, gave stereoselectively 2,5-cis-disubstituted 3(2H)-furanone. The furanone was converted to chiral β-hydroxy acid with high optical purity.
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Research Products
(22 results)
