| Project/Area Number |
14572021
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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 | Kyoto Pharmaceutical University |
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Principal Investigator |
YAKURA Takayuki Kyoto Pharmaceutical University, Faculty of Pharmaceutical Sciences, Assistant Professor, 薬学部, 講師 (70220126)
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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 |
¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 2003: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 2002: ¥1,600,000 (Direct Cost: ¥1,600,000)
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| Keywords | discodermolide / laulimalide / microtubule-stabilizing agents / formal synthesis / パラジウム触媒 / ジアゾケトン / 銅触媒 / 形式合成 / オキソニウムイリド / [3,3]-シグマトロピー転位 / 微小管安定化剤 / (R)-リンゴ酸 / 立体選択的 / Baeyer-Villiger反応 / 無溶媒反応 |
|---|
| Research Abstract |
Formal syntheses of microtubule-stabilizing agents, discodermolide and laulimalide were achieved.
Synthesis of discodermolide was started from dimethyl (R)-malate by using chemo-and stereoselective dirhodium catalyzed C-H insertion reaction and novel acceleration technique of Baeyer-Villiger reaction of sterically hindered ketones as key steps to give (2S)-2-tert-butyldimethylsilyloxy-3-[(2S,3S,4S,5R)-4-tert-butyldimethyl-silyloxy-3, 5-dimethyl-6-oxotrahydropyran-2-yl]propanal, Smiths intermediate of their total synthesis of discodermolide. Formal synthesis of laulimalide was included oxonium ylide formation-[3,3]-sigmatropic rearrangement reaction and SN type cyclization as key steps.
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