Total synthesis of natural products by organocatalytic construction of all-carbon quaternary stereocenter
| Project/Area Number |
16K17903
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Synthetic chemistry
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| Research Institution | Meijo University (2017-2018)
Kyoto University (2016) |
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Principal Investigator |
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Project Status |
Completed (Fiscal Year 2018)
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| Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2018: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
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| Keywords | 有機合成化学 / 天然物化学 / 有機触媒 / 全合成 / 有機分子触媒 / 不斉反応 / 天然物合成 / 不斉4級炭素 |
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| Outline of Final Research Achievements |
There are many natural products and drugs including chiral spiro-ring. However, the construction of spiro-ring containing a quaternary carbon is more difficult than the spiro ring having a hetero atom. In our laboratory, we developed the new method using organocatalyst to construct the all-carbon quaternary stereocenter or tetrasubstituted carbon by intramolecular Friedel-Crafts type 1.4 addition reaction and oxy-Michel addition. Furthermore, we succeeded to apply these reactions into the total synthesis of (-)-misramine and（-)-(R)-cordiachromene.
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| Academic Significance and Societal Importance of the Research Achievements |
申請者の開発した有機分子触媒によるエナンチオ選択的な不斉四級炭素構築法は、これまで光学活性体の合成報告例のない不斉四級炭素含有天然物が効率的に構築できる。そのため、天然からの供給が少なく、いまだ生物活性の報告例がない各種類縁体の合成が可能であり、新たな活性の発見や、医薬品シード化合物探索としての展開が期待できる。
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Report
(4 results)
Research Products
(45 results)
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[Journal Article] Total Synthesis of Clavilactones2018
Author(s)
Ken-ichi Takao, Kento Mori, Kenya Kasuga, Ryuki Nanamiya, Ayumi Namba, Yuuki Fukushima, Ryuichi Nemoto, Takuma Mogi, Hiroyuki Yasui, Akihiro Ogura, Keisuke Yoshida, Kin-ichi Tadano
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Journal Title
The Journal of Organic Chemistry
Volume: 83
Issue: 13
Pages: 7060-7075
DOI
Related Report
Peer Reviewed
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