Concise Synthesis and Skeletal Diversification of Natural Products and their Variants Employing a Multipotent Intermediate.
| Project/Area Number |
15H03117
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical biology
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| Research Institution | Tokyo University of Agriculture and Technology |
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Principal Investigator |
OGURI HIROKI 東京農工大学, 工学(系)研究科(研究院), 教授 (80311546)
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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 |
¥17,420,000 (Direct Cost: ¥13,400,000、Indirect Cost: ¥4,020,000)
Fiscal Year 2017: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2016: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2015: ¥7,800,000 (Direct Cost: ¥6,000,000、Indirect Cost: ¥1,800,000)
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| Keywords | アルカロイド / 骨格多様化合成 / 多能性中間体 / ジヒドロピリジン / 生合成摸倣合成 / 骨格多様化 / 生合成摸倣 / 二量化反応 / 環化反応 / 生理活性 / 有機合成化学 / 天然物化学 / シアノメチル化 / アリル化 / テトラヒドロピリジン / 合成化学 / 天然物 / 分子設計 / 環化 / ピペリジン |
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| Outline of Final Research Achievements |
Exploiting a carbonyl group installed at the C3 position of the 1,6-dihydropyridine (DHP) system, we devised a strategy for cyanomethylation at C2/C6 and subsequent divergent installation of an allyl group at C3/C5 in a highly regio- and stereo-controlled manner. Installation of the gem-dimethyl groups at C6 positions could inhibit disproportionation and allowed region-controlled dimerization gaining a concise access to a halicyclamine-type skeleton.
Intramolecular hydroarylations of N-propargylated tetrahydrocarbolines were efficiently mediated by Zn(OTf)2. We systematically implemented divergent annulations involving two kinds of ring-expansion reactions and spirocyclizations that efficiently generated three distinct alkaloidal scaffolds. Furthermore, we found intriguing solvent effects of t-BuOH.
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Report
(4 results)
Research Products
(28 results)
