Total synthesis of indole alkaloids containing an indoline spiroaminal framework and evaluation of their anti-infectious activity
| Project/Area Number |
25860010
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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 | Kitasato University |
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Principal Investigator |
YAMADA Takeshi 北里大学, 大学院感染制御科学府, 助教 (00608367)
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| Project Period (FY) |
2013-04-01 – 2015-03-31
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| Project Status |
Completed (Fiscal Year 2014)
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| Budget Amount *help |
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
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| Keywords | 全合成 / インドール / ニトロン / 抗トリパノソーマ / イソシアニド / α-ヒドロキシアミド / ピリドン / αーヒドロキシアミド |
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| Outline of Final Research Achievements |
Total synthesis of the indole alkaloids, neoxaline, oxaline and meleagrin A, all containing a unique indoline spiroaminal framework was accomplished through the stereoselective introduction of a reverse-prenyl group to the congesting benzylic carbon of furoindoline, 2-pot transformation of indoline, containing three nitrogen atoms at appropriate positions, to the featured indoline spiroaminal framework and elimination of carbonate assisted by the adjacent imidazole moiety to construct the (E)-dehydrohistidine. The absolute stereochemistry of the neoxaline was elucidated via our total synthesis. Bioactivity screening indicated that some synthetic intermediates exhibited efficacy against Sleeping Sickness parasites (Trypanosoma brucei brucei ) .
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Report
(3 results)
Research Products
(19 results)
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[Journal Article] Asymmetric total synthesis of neoxaline2013
Author(s)
Tetsuya Ideguchi, Takeshi Yamada, Tatsuya Shirahata, Tomoyasu Hirose, Akihiro Sugawara, Yoshinori Kobayashi, Satoshi Omura, Toshiaki Sunazuka
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Journal Title
J Am Chem Soc
Volume: 135
Issue: 34
Pages: 12568-12571
DOI
Related Report
Peer Reviewed
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[Presentation] Concise Asymmetric Total Synthesis of Neoxaline Family2014
Author(s)
Tetsuya Ideguchi, Takeshi Yamada, Tatsuya Shirahata, Tomoyasu Hirose, Akihiro Sugawara, Yoshinori Kobayashi, Satoshi Omura, Toshiaki Sunazuka
Organizer
Advanced Molecular Transformation by Organocatalysts 2nd International Conference & 7th Symposium on Organocatalysis
Place of Presentation
Bunkyo-ku, Tokyo, Tokyo University
Year and Date
2014-11-21 – 2014-11-22
Related Report
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[Presentation] Asymmetric Total Synthesis of (+)-Neoxaline2013
Author(s)
Tetsuya Ideguchi, Takeshi Yamada, Tatsuya Shirahata, Tomoyasu Hirose, Akihiro Sugawara, Yoshinori Kobayashi, Satoshi Omura, Toshiaki Sunazuka
Organizer
13th International Conference on the Chemistry of Antibiotics and bioactive compounds (ICCA-13)
Place of Presentation
Fuji view hotel, Yamanashi
Related Report
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