Development of new radical chemistry-based strategies for the construction of densely functionalized organic molecules
Project/Area Number |
21590009
|
Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Single-year Grants |
Section | 一般 |
Research Field |
Chemical pharmacy
|
Research Institution | Osaka University |
Principal Investigator |
|
Project Period (FY) |
2009 – 2012
|
Project Status |
Completed (Fiscal Year 2012)
|
Budget Amount *help |
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2011: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2009: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
|
Keywords | 全合成 / ラジカル / 生物活性天然物 / 炭素-水素(C-H)結合変換 / 創薬 / ラジカル反応 / C-H 変換 / アルカロイド / 抗生物質 / 合成戦略 / C-H変換 |
Research Abstract |
Bioactive natural products often possess unique chemical structures with dense functionalities, serving as a useful medicinal resource. The authors have been engaged in synthetic radical chemistry that would revolutionize strategies for providing access to this class of attractive molecules. In the present study, we succeeded in devising new radical reactions associated with sp3carbon-hydrogen (sp3C-H) transformation (photochemical sp3C-H carbamoylation of tertiary amines) and iron(II)-catalyzed aminohalogenation reactions of N-tosyloxycarbamates, and accomplished radical chemistry-based total syntheses of bioactive natural products including kainic acid, platencin, and agelastatin A. Furthermore, we developed a novel means for asymmetric synthesis, which employsremote stereoinduction that allows facile construction of carbocyclic building blocks bearing quaternary stereocenters. The biological evaluation of platencin prepared by the above-mentioned total synthesishas allowed the authors to assess its significant inhibitory activity against multi-drug-resistant Mycobacterium tuberculosis, adding a new dimension to the development of antitubercular agents.
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Report
(4 results)
Research Products
(96 results)
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[Presentation] カイニン酸の全合成2011
Author(s)
家門拓麻、入船弥生、田中徹明、 好光健彦
Organizer
第37回反応と合成の進歩シンポジウム
Place of Presentation
徳島
Year and Date
2011-11-07
Related Report
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[Presentation] カイニン酸の全合成2011
Author(s)
家門拓麻、入船弥生、田中徹明、 好光健彦
Organizer
第41回複素環化学討論会会
Place of Presentation
熊本
Year and Date
2011-10-20
Related Report
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[Presentation] カイニン酸の全合成2011
Author(s)
家門拓麻、入船弥生、田中徹明、 好光健彦
Organizer
第53回天然有機化合物討論会
Place of Presentation
大阪
Year and Date
2011-09-28
Related Report
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[Presentation] カイニン酸の全合成2011
Author(s)
家門拓麻、入船弥生、田中徹明、 好光健彦
Organizer
第9回次世代を担う有機化学シンポジウム
Place of Presentation
東京
Year and Date
2011-05-27
Related Report
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