| Project/Area Number |
21790012
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kanazawa University |
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Principal Investigator |
INAGAKI Fuyuhiko Kanazawa University, 薬学系, 助教 (80506816)
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| Project Period (FY) |
2009 – 2010
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| Project Status |
Completed (Fiscal Year 2010)
|
| Budget Amount *help |
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2010: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2009: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
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| Keywords | 有機化学 / ナカドマリンA / Pauson-Khand 反応 / 天然物合成 / アレン / Pauson-Khand / Pauson-Khand反応 |
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| Research Abstract |
We completed the total synthesis of (+)-nakadomarin in a highly stereoselectve manner from the commercially available L-pyroglutamic acid. The most significant point of this synthesis involves the intramolecular Pauson-Khand reaction between the alkyne and N-protected-dihydropyrrole functionalities, which enabled us to construct the diazatricyclo[6.4.0.0^<1,5>]dodcadienone product. This reaction was also useful for the short-step synthesis of (±)-meloscine. In addition, we succeeded to extend the application of the rhodium catalyzed Pauson-Khand type reaction of allenenes for the construction of bicyclo[4.3.0] skeletons containing quaternary carbon at the ring juncture. This method provided a new procedure for the construction of the tricyclo[6.4.0.0^<1,5>]dodecenone framework in a satisfactory yield.
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