Establishment of novel synthetic strategy utilizing two types of photo-induced direct C(sp3)-H functionalization.
| Project/Area Number |
26860009
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Chemical pharmacy
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| Research Institution | The University of Tokyo |
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Principal Investigator |
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| Project Period (FY) |
2014-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2014: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
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| Keywords | 直截的変換反応 / 全合成 / 光化学反応 / 不斉アルキニル化反応 / ラクタシスチン / 20Sプロテアソーム阻害活性 / ザラゴジン酸C / 高脂血症治療薬 / 光反応 / C(sp3)-H直接官能基化 / フローリアクター / 発光ダイオード / オオムラリド / 青色発光ダイオード |
|---|
| Outline of Final Research Achievements |
Development of direct transformations of C-H bonds has attracted intense attention from chemical community. We particularly focus on C(sp3)-H bond oxidations and functionalizations of multiply substituted carboskeletons.
This time we have achieved the following three research results. 1) Enantioselective alkynylation of C(sp3)-H bonds adjacent to a nitrogen atom has been achieved using only chiral p-tolyl tert-butyldimethylsilylethynyl sulfoximine and benzophenone under photo-irradiation conditions. 2) Total synthesis of (+)-lactacystin, a potent inhibitor of the 20S proteasome has been achieved using the chemo- and stereoselective photoinduced intermolecular C(sp3)-H alkynylation and intramolecular C(sp3)-H acylation. 3) Total synthesis of (+)-zaragozic acid C, having inhibitory activity of mammalian squalene synthase, has been achieved using the chemo- and stereoselective photoinduced intramolecular C(sp3)-H acylation.
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Report
(3 results)
Research Products
(33 results)
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[Journal Article] Total Synthesis of Ryanodol2014
Author(s)
Masanori Nagatomo, Masaki Koshimizu, Kengo Masuda, Toshiki Tabuchi, Daisuke Urabe, Masayuki Inoue
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Journal Title
Journal of the American Chemical Society
Volume: 136
Issue: 16
Pages: 5916-5919
DOI
Related Report
Peer Reviewed
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[Presentation] クラジェリン類の合成研究2016
Author(s)
増田圭佑、長友優典、井上将行
Organizer
日本薬学会 第136年会
Place of Presentation
パシフィコ横浜（神奈川県・横浜市）
Year and Date
2016-03-26
Related Report
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[Presentation] リアノイド類の網羅的全合成2015
Author(s)
小清水正樹、長友優典、井上将行
Organizer
第57回天然有機化合物討論会
Place of Presentation
神奈川県民ホール（神奈川県・横浜市）
Year and Date
2015-09-09
Related Report
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[Presentation] (+)-リアノジンの不斉全合成2014
Author(s)
枡田健吾, 長友優典, 小清水正樹, 萩原幸司, 田渕俊樹, 占部大介, 井上将行
Organizer
第56回天然有機化合物討論会
Place of Presentation
高知県民文化ホール
Year and Date
2014-10-15 – 2014-10-17
Related Report
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[Presentation] リアノドールの全合成2014
Author(s)
小清水正樹, 長友優典, 枡田健吾, 萩原幸司, 田渕俊樹, 占部大介, 井上将行
Organizer
第31回有機合成化学セミナー
Place of Presentation
休暇村 志賀島（福岡県福岡市東区大字勝馬）
Year and Date
2014-09-17 – 2014-09-19
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[Presentation] (±)-リアノドールの全合成2014
Author(s)
小清水正樹, 長友優典, 枡田健吾, 田渕俊樹, 占部大介, 井上将行
Organizer
第12回次世代を担う有機化学シンポジウム
Place of Presentation
日本薬学会長井記念ホール
Year and Date
2014-05-23 – 2014-05-24
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