1995 Fiscal Year Final Research Report Summary
Development of New Synthetic Methods for the Preparation of Organic Fluorine Compounds and the Application to Fluorinated Biological Substances
| Project/Area Number |
06672113
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Tokyo College of Pharmacy |
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Principal Investigator |
TAGUCHI Takeo Tokyo College of Pharmacy, School of Pharmaceutical Science, Professor, 薬学部, 教授 (00016180)
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| Co-Investigator(Kenkyū-buntansha) |
KATAGAWA Osamu Tokyo College of Pharmacy, School of Pharmaceutical Science, Lecturer, 薬学部, 講師 (30214787)
MORIKAWA Tsutomu Tokyo College of Pharmacy, School of Pharmaceutical Science, Lecturer, 薬学部, 講師 (40166393)
HANZAWA Yuji Tokyo College of Pharmacy, School of Pharmaceutical Science, Associate Professor, 薬学部, 助教授 (10096688)
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| Project Period (FY) |
1994 – 1995
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| Keywords | Cyclopropane / Difluorocycloprepane / Glutamic acid / Difluoroketone / Asymmetric synthesis / Zirconium complex / Diels-Alder reaction / Iodine |
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| Research Abstract |
1. Development of Asymmetric Synthesis of Difluorocyclopropanes and Its Application to Chemical Modification of Glutamic Acid
Introduction of cyclopropane unit into a molecule is recognized as an important molecular design in the field of medicinal chemistry and material sciences. We have developed efficient methods for asymmetric synthesis of fluorinated cyclopropanes directed toward chemical modification of biologically important substances. We have successfully established two methods, namely (1) diastereo-, regio- and stereo-selective synthesis of functionalized difluorocyclopropaned using bromodifluorocrotonate and (2) preparation of chiral building blocks using difluorocarbene addition reaction. Furthermore, we have achieved the synthesis of all of the possible stereoisomers of (difluoromethano) glutamates and we have also found a new specific agonit for metabotropic glutamate receptor.
2. Development of Aldor-type Reaction of Difluoroviny Ether Derivatives
For the prepartion of fun
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ctionalized difluoroketones, which are classified as important compounds as inhibitors of certain hydrolytic enzymes, we have succeeded in developing efficient aldol-type reactions of difluorovinyl ether derivatives with carbonyl and imine compounds through new activing processes.
3. Developments of Synthetic Methods Based on Zirconocene Chemistry
In our ongoing research project on zirconocene chemistry, we have established an efficient method for the construction of steroidal side chain based on the reaction of zirconocene with vinylcyclopropane, and we have also studied a short-step construction of steroidal skeleton based on the reaction of zirconocene and alkoxymethylated stirene derivatives.
4. Development of New Synthetic Reactions Through Electrophilic Iodination
As an efficient synthetic reaction related to our research project on iodine-mediated activaing process, we have established Diels-Alder reaction of N-allylic enamides. Furthermore, we have succeeded in asymmetric catalysis of our iodocarbocyclization reaction.
Application of our newly developed zirconocene chemistry and iodine-mediated reactions to fluorine chemistry ia our ongoing subject. Less
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Research Products
(34 results)
