2003 Fiscal Year Final Research Report Summary
Development of new synthetic methods for organofluorine compounds of biomedical interest
| Project/Area Number |
13672231
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Tokyo University of Pharmacy and Life Science |
|---|
Principal Investigator |
TAGUCHI Takeo Tokyo University of Pharmacy and Life Science, School of Pharmacy, Professor, 薬学部, 教授 (00016180)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
ITO Hisanaka Tokyo University of Pharmacy and Life Science, School of Pharmacy, Lecturer, 生命科学部, 講師 (70287457)
KITAGAWA Osamu Tokyo University of Pharmacy and Life Science, School of Pharmacy, Lecturer, 薬学部, 講師 (30214787)
|
|---|
| Project Period (FY) |
2001 – 2003
|
| Keywords | Fluorinated olefins / Dipeptide isostere / carbocyclization / Cyclopropane derivative / Radical cycloaddition / Homoally radical |
|---|
| Research Abstract |
As our continuous studies on development of new synthetic methods for organofluorine compounds directed to the synthesis of fluoro analogs of biomedically interesting compounds, we have focused to develop efficient methods for stereoselective construction of fluorinated olefins, carbocyclic compounds and cyclopropane carboxylic acid derivatives during these three years with the financial support in part from the Ministry of Education, Science, Sports and Culture. Our achievements in fluorine chemistry are summarized as follows. (1)Stereoselective construction of (Z)-fluoroolefin derivatives having an appropriate functional groups and substituents, which can be applied as dipeptide isosteres can be established. (2)We have developed carbocyclization reaction of terminally difluorinated alkenyl active methine compounds leading to fluorinated functionalized five membered carbocylic compounds. (3)A two step stereoselective synthesis of fluorocyclopropane carboxylic acid derivatives was successfully established. Moreover, development of highly efficient synthetic methods for nonfluorinated organic compounds, which, due to their generality, could be applied to the preparation of fluorinated compounds in the future is also involved in our research project. These are radical [3+2] cycloaddition reactions of homoallyl active methine radical species and azahomoallyl radical species with various alkenes leading to the coresponding cyclic compounds, and zirconium mediated olefin-carbonyl coupling reaction of N-alkenylcarbamate derivatives for the preparation of amino acids and nitrogen containing heterocyclic compounds.
|
-
-
-
-
-
-
[Publications] Okada, M., Nakamura, Y., Saito, A., Sato, A., Horikawa, H., Taguchi, T.: "Synthesis of α-Alkylated (Z)-γ-Fluoro-β,γ-enoates through Organocopper Mediated Reaction of γ,γ-Difluoro-α,β-enoates : A Different Reactivity of R_3Al-Cu(I) and Me_2CuLi."Chem.Lett.. 28-29 (2002)
Description
「研究成果報告書概要(欧文)」より
-
[Publications] Okada, M., Nakamura, Y., Saito, A., Sato, A., Horikawa, H., Taguchi, T.: "Stereoselective construction of functionalized (Z)-fluoroalkenes directed to depsipeptide isosteres."Tetrahedron Lett.. 43. 5845-5847 (2002)
Description
「研究成果報告書概要(欧文)」より
-
[Publications] Saito, A., Okada, M., Nakamura, Y., Kitagawa, O., Horikawa, H., Taguchi, T.: "Carbocyclization reactions of terminally difluorinated alkenyl active methine compounds mediated by SnCl_4 and amine."J.Fluorine Chem.. 123. 75-80 (2003)
Description
「研究成果報告書概要(欧文)」より
-
-
-
[Publications] Kitagawa, O., Yamada, Y., Fujiwara, H., Taguchi, T.: "Radical Cascade Reaction with 1,4-Dienes and 1,4-Enynes Using 2-(lodomethyl)cyclopropane-1,1-dicarboxylate as a Homoallyl Radical Precursor : One-Step Synthesis of Bicyclo[3.3.0]octane Derivatives."J.Org.Chem.. 67. 933-927 (2002)
Description
「研究成果報告書概要(欧文)」より
-
-
-
-
-
-
