Development of Frieden-Crafts type reactions and their applications to heterocyclic molecule syntheses
| Project/Area Number |
15K07850
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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 | Chiba University |
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Principal Investigator |
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| Project Period (FY) |
2015-04-01 – 2018-03-31
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| Project Status |
Completed (Fiscal Year 2017)
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| Budget Amount *help |
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
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| Keywords | Friedel-Crafts反応 / 脱芳香化 / インドール / 天然物合成 / 銀カルベノイド / フリーデルクラフツ反応 / カスケード反応 / パラジウム / フリーデルークラフツ反応 / 遷移金属触媒 / プラチナ |
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| Outline of Final Research Achievements |
We developed the following synthetic methods in this study. (1) We developed a silver-caebenoid mediate ipso-Friedel-Crafts type intramolecular dearomatization of phenols. This process could be extended to the asymmetric reaction using chiral phosphoric acid ligands. (2) We developed a synthetic method of 3,4-fused tricyclic indole derivatives using 3,4-fused 3-alkylidene indolines as their precursors. Two types of cascade processes were developed based on palladium catalysis and platinum catalysis. (3) Using the developed methods, we succeeded in the total synthesis of (-)-aurantioclavine and fargesine. Synthetic studies of dragmacidin E were also examined using the developed palladium catalysis. In addition, we developed a synthetic method of 3,4-fused tetrahydrobenzopyranes using para-quinonemethides as key intermediates.
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Report
(4 results)
Research Products
(34 results)
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[Journal Article] Platinum-Catalyzed Friedel-Crafts-Type C–H Coupling–Allylic Amination Cascade to Synthesize 3,4-Fused Tricyclic Indoles2016
Author(s)
Yuta Suzuki, Yuito Tanaka, Shun-ichi Nakano, Kousuke Dodo, Natsumi Yoda, Ken-ichi Shinohara, Kazuko Kita, Atushi Kaneda, Mikiko Sodeoka, Yasumasa Hamada, and Tetsuhiro Nemoto
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Journal Title
Chem. Eur. J.
Volume: 22
Issue: 13
Pages: 4418-4421
DOI
Related Report
Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
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