| Project/Area Number |
09555285
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 展開研究 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Toyohashi University of Technology |
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Principal Investigator |
NISHIYAMA Hisao Toyohashi University of Technology, 工学部, 教授 (40135421)
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| Co-Investigator(Kenkyū-buntansha) |
NAGASE Hiroshi 東レ株式会社, 基礎研究所, 副長所
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| Project Period (FY) |
1997 – 1999
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| Project Status |
Completed (Fiscal Year 1999)
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| Budget Amount *help |
¥11,700,000 (Direct Cost: ¥11,700,000)
Fiscal Year 1999: ¥2,600,000 (Direct Cost: ¥2,600,000)
Fiscal Year 1998: ¥3,900,000 (Direct Cost: ¥3,900,000)
Fiscal Year 1997: ¥5,200,000 (Direct Cost: ¥5,200,000)
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| Keywords | asymmetric reaction / prostacyclin / organometallics / desymmetrization / cyclopentenediol / asymmetric induction / ラジカル還元 / プロスタグランジン / 非対称化 / ベンゾフラン / 不斉誘導 / リチウム塩 |
|---|
| Research Abstract |
New asymmetric reaction and desymmetrization method have been applied in synthetic routes for bioactive prostaglandin derivative such as prostacyclin (PGI2), which is expected as an anti-platelet drugs. First, bis (boromophenoxy) cyclopentene derivatives were examined to SN2' reaction with Grignard reagents in metal-halogen exchange and subsequent cyclization to give a precursor of prostacyclin. An authentic sample of desired compound was synthesized from optically active cycopentanediol derivative by the desymmetric process. Second, meso-diacetoxy-cyclopentene was subjected to enantioselective desymmetric cyclization with chiral palladium catalyst to give the desired cyclization product as a precorsor in over 95% ee in high yield. Finally, above process was applied for optically active prostacycline, chiral Beraprost. In addition, non chiral Beraprost was also synthesized via new several routes.
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