| Project/Area Number |
14572005
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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 | Osaka University |
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Principal Investigator |
FUJIOKA Hiromichi Osaka University, Graduate School of Pharmaceutical Sciences, Associate Professor, 薬学研究科, 助教授 (10173410)
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| Project Period (FY) |
2002 – 2003
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| Project Status |
Completed (Fiscal Year 2003)
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| Budget Amount *help |
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2003: ¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 2002: ¥1,800,000 (Direct Cost: ¥1,800,000)
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| Keywords | (R, R)-hydrobenzoin / asymmetric desymmetrization / stenine / scyphostatin / acyclic σ-symmetic diene acetal / domino haloetherification / optically active tetrahydrofuran / シクロヘキサジエンアセタール / 3-エンドフェニルノルボルネンアルデヒド / メソ-ジオール |
|---|
| Research Abstract |
Formations of chiral oxonium ion intermediates by intramolecular haloetherification of ene acetals and their applications have been investigated.
As an application of the chiral, non-racemic cyclohexene acetal obtained by an intramolecular haloetherification reaction of cyclohexadiene acetal from 3-(1,4-cyclohaxadien-3-yl)propanal and chiral hydrohenzoin, synthetic work of stemona alkaloids was held. As a result, 9a-epi-stenine has been achieved, and the synthesis of stenine itself is on the last stage. From the intermediate of their syntheses, the epoxy cyclohexenone core of scyphostatin having N-Smase inhibiting activity was synthesized.
Furthermore, an unexpected domino intramolecular haloetherification reaction of acyclic σ-symmetic diene acetals was found, and the tetrahyderofurans having four asymmetric centers were obtained in one-pot operation.
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