Development of Efficient Synthetic Transformation based on Intramolecular Redox Reaction
| Project/Area Number |
24350021
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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 |
Organic chemistry
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| Research Institution | Tokyo Institute of Technology |
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Principal Investigator |
Ohmori Ken 東京工業大学, 理工学研究科, 准教授 (50282819)
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| Co-Investigator(Renkei-kenkyūsha) |
SUZUKI Keisuke 東京工業大学, 大学院理工学研究科, 教授 (90162940)
ANDO Yoshio 東京工業大学, 大学院理工学研究科, 助教 (40532742)
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| Project Period (FY) |
2012-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥18,330,000 (Direct Cost: ¥14,100,000、Indirect Cost: ¥4,230,000)
Fiscal Year 2014: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2013: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2012: ¥7,410,000 (Direct Cost: ¥5,700,000、Indirect Cost: ¥1,710,000)
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| Keywords | 有機合成 / 酸化還元反応 / レドックス反応 / 分子内反応 / 酸化 / 還元 / アレン / 光反応 / レドックス / 天然有機化合物 / 熱反応 / 全合成 / スピロキシン / ニトロン |
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| Outline of Final Research Achievements |
This research project focused on development of new synthetic strategy and tactics focusing on intra-molecular redox transformations. Three research topics are addressed. At first, retro-[4+2] cycloaddition reaction for enolsilyl ether of dioxinone derivative was studied. The planned reaction proved feasible by heating of the substrate in toluene or xylene, giving the corresponding allene derivatives in moderate to high yield. In second, reaction of allenes and nitrones were studied. Upon heating of the allenes with nitrones underwent unusual homolytic N-O bond cleavage followed by recombination of resulting radicals to form a C-C bond, affording the corresponding lactams albeit in low yields. This research has been also studied intramolecular redox reaction of naphthoquinone derivatives, enabling construction of a new heterocyclic ring, typically furan ring skeletons. This method would serve as an efficient way to synthesize various polycyclic compounds.
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Report
(5 results)
Research Products
(13 results)
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[Presentation] スピロキシンAの合成研究2015
Author(s)
佐々木亮太、安藤吉勇、大森建、鈴木啓介
Organizer
日本化学会第９５回春季年会
Place of Presentation
日本大学・船橋キャンパス
Year and Date
2015-03-28
Related Report
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