1999 Fiscal Year Final Research Report Summary
Synthesis of Cyclic Amino Acids Aiming at Elucidation of Neurotransmission Mechanism
| Project/Area Number |
09672293
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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 |
医薬分子機能学
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| Research Institution | Kobe Pharmaceutical University |
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Principal Investigator |
NAITO Takeaki Kobe Pharmaceutical University, Professor, 薬学部, 教授 (00068339)
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| Co-Investigator(Kenkyū-buntansha) |
MIYABE Hideto Kobe Pharmaceutical University, Assistant, 薬学部, 助手 (10289035)
MIYATA Okiko Kobe Pharmaceutical University, Lecturer, 薬学部, 講師 (90102110)
KIGUCHI Toshiko Kobe Pharmaceutical University, Associate Professor, 薬学部, 助教授 (70068344)
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| Project Period (FY) |
1997 – 1999
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| Keywords | neurotransmission mechanism / Kainic acid / amino acid / radical / thiophenol / cyclization / dipolar cycloaddition |
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| Research Abstract |
Aiming at elucidation of neurotransmission mechanism involving amino acids, we started to develop a novel cyclization reactions suitable for the practical synthesis of cyclic amino acids which would be employed as crucial tools for the mechanistic study on neurotransmitters. Thus, ecological thiyl radical addition-cyclization of carbon multiple bonds and stannyl radical addition-cyclization of the carbonyl group have been proved to be potential synthetic method for the cyclic amino acids.
1. Thiyl Radical Addition-Cyclization and its Application to the Synthesis of Cyclic Amino Acids
Readily available oxime ethers were subjected to thiyl radical addition-cyclization to give the adjacently functionalized cyclic compounds which were effectively converted into carbocyclic and heterocyclic amino acids. Asymmetric synthesis of (-)-α-kainic acid was achieved by applying newly found thiyl radical addition-cyclization-elimination reacting using a catalytic amount of thiophenol.
2. 1,3-Dipolar Cycloaddition of Nitrone and its Application to the Synthesis of Cyclic Amino Acids
Combination of 1,3-dipolar cycloaddition of nitrones to chiral olefin and the following ring conversion were successfully applied the synthesis of azimic acid which is component of macrolide amino lactone, azimine, and expected to be active in central nervous system.
3. Stannyl Radical Addition-Cyclization and its Application to the Synthesis of Cyclic Amino acids.
We developed stannyl radical addition-cyclization of oxime ethers connected with the carbonyl groups and application to the synthesis of cyclic amino acids and the related compounds such as (-)-balanol.
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