2017 Fiscal Year Final Research Report
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 |
Section | 一般 |
Research Field |
Chemical biology
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Research Institution | Tokyo University of Agriculture and Technology |
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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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 |
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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Free Research Field |
有機合成化学
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