Stereoselective Synthesis of Cyclic Alkaloids Using the Cation Pool Method
| Project/Area Number |
25410117
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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 |
Synthetic chemistry
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| Research Institution | Okayama University |
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Principal Investigator |
SUGA SEIJI 岡山大学, 自然科学研究科, 教授 (50291430)
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| Project Period (FY) |
2013-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | 選択的合成 / イミニウムカチオン / アルカロイド / カチオンプール法 / 電解酸化 / 立体選択的反応 / NMR |
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| Outline of Final Research Achievements |
The purpose of the present research is to reveal the mechanistic insight of diastereoselective synthesis of di-substituted piperidine derivatives accomplished by the reaction of N-acyliminium ions, which are prepared by the Indirect Cation Pool Method. The reactions of highly reactive N-acyliminium ions having a piperidine skeleton with a substituent, generated and accumulated from the corresponding thioaminals by the treatment of electrochemically generated arylsulfonium ion pool, with carbon nucleophiles gave rise to the formation of the corresponding of di-substituted piperidine derivatives in a highly-stereoselective manner. We validated the relationship of the conformations of cationic intermediates and stereoselectivities. The conformations of the N-acyliminium ions were determined by NMR spectroscopy, and the origin of the stereoselectivity was mostly clarified.
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Report
(4 results)
Research Products
(54 results)
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[Journal Article] Facile Synthesis of 1,4-Bis(diaryl)-1,3-butadiynes Bearing Two Amino Moieties by Electrochemical Reaction Site Switching, and Their Solvatochromic Fluorescence2016
Author(s)
N. Kamimoto, N. Nakamura, A. Tsutsumi, H. Mandai,K. Mistudo, A. Wakamiya, Y. Murata, J. Hasegawa, and S. Suga
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Journal Title
Asian J. Org. Chem.
Volume: 5
Issue: 3
Pages: 373-379
DOI
Related Report
Peer Reviewed
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[Journal Article] Synthetic (+)-Terrein Suppresses Interleukin-6/soluble Intereleukin-6 Receptor Induced-secretion of Vascular Endothelial Growth Factor in Human Gingival Fibroblasts2014
Author(s)
Mandai,H.; Omori, K.; Yamamoto, D.; Tsumura, T.; Murota, K.; Yamamoto, S.; Mitsudo, K.; Ibaragi, S.; Sasaki, A.; Maeda, H.; Takashiba, S.; Suga, S.
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Journal Title
Bioorg. & Med. Chem.
Volume: 22
Issue: 19
Pages: 5338-5344
DOI
Related Report
Peer Reviewed / Open Access
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