2017 Fiscal Year Final Research Report
Synthetic study of polycyclic natural products with multi-quaternary asymmetric carbon atoms: development of synthetic strategies and elucidation of biological effects
| Project/Area Number |
15K01795
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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 |
Biomolecular chemistry
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| Research Institution | University of Shizuoka (2017)
Hokkaido University (2015-2016) |
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Principal Investigator |
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| Project Period (FY) |
2015-04-01 – 2018-03-31
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| Keywords | 全合成 / アンドラスチン / ブラシリカルジン / ニトリル / 四級不斉炭素 / N-シリルケテンイミン / アリールアミン / 電子環状反応 |
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| Outline of Final Research Achievements |
This research aimed at total syntheses of Andrastin C, Brasilicardin A, and Portulal that belong to biologically active natural products with multi-quaternary asymmetric carbon atoms on their polycyclic frameworks. To achieve this goal, novel method for stereoselective construction of a quaternary asymmetric carbon atom was developed by using an intramolecular conjugate addition reaction of an unsaturated Weinreb amide. By using this reaction as key reactions, we succeeded in the asymmetric synthesis of Brasilicardin A. In addition, we achieved the stereoselective synthesis of the AB-ring and BCD-ring moieties of Andrastin C, in which the latter possesses three consecutive quaternary asymmetric carbon atoms. Furthermore, we developed new carbon-carbon bond-forming reactions, which proceed via the formation of an N-silyl ketene imine intermediate generated in situ.
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| Free Research Field |
有機合成化学
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