Organic synthesis of functional polycyclic compounds with ynolates
| Project/Area Number |
26293004
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Partial Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kyushu University |
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Principal Investigator |
SHINDO MITSURU 九州大学, 先導物質化学研究所, 教授 (40226345)
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| Co-Investigator(Kenkyū-buntansha) |
岩田 隆幸 九州大学, 先導物質化学研究所, 助教 (00781973)
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥16,900,000 (Direct Cost: ¥13,000,000、Indirect Cost: ¥3,900,000)
Fiscal Year 2016: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2015: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2014: ¥7,150,000 (Direct Cost: ¥5,500,000、Indirect Cost: ¥1,650,000)
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| Keywords | 有機化学 / 多環化合物 / フローリアクター / イノラート / トリプチセン / 全合成 / アルカロイド / 連続反応 / フロー合成 / 有機合成化学 |
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| Outline of Final Research Achievements |
We developed the novel one-pot synthetic method of substituted triptycenes by the reaction of ynolates and arynes. This four-step process involves three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucleophiles (ynolate, enolate, and anthracenolate) reacts with o-benzyne in the same predictable manner controlled by chelation and negative hyperconjugation. The resulting functionalized C3-symmetrical triptycenes hold promise in the design of functional materials.
The first heterogeneously catalyzed oxidative dehydrogenative homo- and cross-coupling of aryl amines, giving biarylamines, was developed.
Asymmetric total synthesis of (-)-stemonamine was achieved by using ynolate-initiated [2+2]cycloaddition-Dieckmann condensation as a key step.
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Report
(4 results)
Research Products
(52 results)
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[Journal Article] Efficient Total Synthesis of Bongkrekic Acid and Apoptosis Inhibitory Activity of its Analogues2015
Author(s)
K. Matsumoto, M. Suyama, S. Fujita, T. Moriwaki, Y. Sato, Y. Aso, S. Muroshita, H. Matsuo, K. Monda, K. Okuda, M. Abe, H. Fukunaga, A. Kano, M. Shindo,*
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Journal Title
Chem. Eur. J.
Volume: 21
Issue: 32
Pages: 11590-11602
DOI
Related Report
Peer Reviewed / Open Access / Acknowledgement Compliant
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[Journal Article] Bongkrekic Acid Analogue, Lacking One of the Carboxylic Groups of its Parent Compound, Shows Moderate but pH-insensitive Inhibitory Effects on the Mitochondrial ADP/ATP Carrier2015
Author(s)
Atsushi Yamamoto, Keisuke Hasui, Hiroshi Matsuo, Katsuhiro Okuda, Masato Abe, Kenji Matsumoto, Kazuki Harada, Yuya Yoshimura, Takenori Yamamoto, Kazuto Ohkura, Mitsuru Shindo, Yasuo Shinohara
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Journal Title
Chem. Biol. Drug Des.
Volume: 86
Issue: 5
Pages: 1304-1322
DOI
NAID
Related Report
Peer Reviewed / Open Access
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[Presentation] 混雑多環化合物の合成2016
Author(s)
新藤充
Organizer
大阪市立大学大学院理学研究科物質分子系専攻談話会
Place of Presentation
大阪市立大学
Year and Date
2016-09-26
Related Report
Invited
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[Presentation] イノラートの化学2014
Author(s)
新藤充
Organizer
有機合成化学協会中国四国支部「化学道場」
Place of Presentation
岡山市
Year and Date
2014-08-30
Related Report
Invited
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[Presentation] アレロパシーの化学2014
Author(s)
新藤充
Organizer
東京工業大学大学院生命理工学専攻講演会
Place of Presentation
東京工業大学長津田キャンパス
Year and Date
2014-06-27
Related Report
Invited
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