2015 Fiscal Year Final Research Report
Development of mild oxidation reaction and its application to total synthesis of highly oxygenated natural products
Project/Area Number |
25460003
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Multi-year Fund |
Section | 一般 |
Research Field |
Chemical pharmacy
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Research Institution | Kobe University (2015) Tohoku University (2013-2014) |
Principal Investigator |
Okano Kentaro 神戸大学, 工学(系)研究科(研究院), 准教授 (30451529)
|
Project Period (FY) |
2013-04-01 – 2016-03-31
|
Keywords | MPC1001 / アコニチン / ジケトピペラジン / 全合成 / マクロラクトン |
Outline of Final Research Achievements |
In this study we accomplished a total synthesis of MPC1001B, antiproliferative activity against DU145 human prostate cancer cell line, based on inversion of the two stereogenic centers that were generated in the key TBAF-mediated formation of the macrolactone. Preliminary experiments on introduction of the hydroxyl group on the dihydrooxepine skeleton for the late-stage oxidation were performed using a model substrate with selenium dioxide to establish mild oxidation conditions. We also investigated construction of the partial skeleton of aconitine through formation of enone from in five steps including Birch reduction. Conversion to the corresponding silyl enol ether followed by Diels-Alder reaction provided the desired tetracyclic compound, which was converted to the secondary alcohol. The mesylate was treated with silica gel to provide the allylic alcohol as a single isomer via Wagner-Meerwein rearrangement. Synthetic studies on acochlearine was also performed.
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Free Research Field |
有機合成化学
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