Stereoselective synthesis of dimeric indole alkaloids utilizing effective construction reaction of quaternary carbon center
| Project/Area Number |
24590032
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Meiji Pharmaceutical University |
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Principal Investigator |
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| Project Period (FY) |
2012-04-01 – 2015-03-31
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| Project Status |
Completed (Fiscal Year 2014)
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| Budget Amount *help |
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
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| Keywords | インドールアルカロイド / 第四級炭素 / ドミノ反応 / 立体選択的反応 / 構造活性相関 / 有機化学 / 合成化学 / 薬学 |
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| Outline of Final Research Achievements |
The synthesis of 2-indolinones including adjacent quaternary carbon centers was performed by the diastereoselective cascade reaction (olefination-isomerization-Claisen rearrangement) of 2-allyloxy-3-indolinones. The scope and limitation of the cascade reaction were defined. By applying this reaction, the construction of backbone architecture having all carbons of natural product communesin F was achieved. The syntheses of phenserine and 5-N-acetylardeemin derivatives and evaluations of their acetyl-/butyryl-cholinesterase and ABCG2-transporter inhibitory were performed to show their structure–activity relationship study (SARS), respectively. The synthetic route to the related compound isoroquefortine was confirmed for its SARS.
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Report
(4 results)
Research Products
(20 results)
