| Budget Amount *help |
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
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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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