2010 Fiscal Year Final Research Report
Study of asymmetric total synthesis of nakadomarin A
| 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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| Keywords | 有機化学 / ナカドマリンA / Pauson-Khand 反応 / 天然物合成 / アレン |
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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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[Journal Article] Org.2011
Author(s)
Inagaki, F., Itoh, N., Hayashi, Y.,Matsui, Y., Mukai, C.,Beilstein J.
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Journal Title
Peer Reviewed
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[Journal Article] Chem.2010
Author(s)
Kawamura, T., Inagaki, F., Narita, S.,Takahashi, Y., Hirata, S., Kitagaki, S.,Mukai, C.
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Journal Title
Eur.J. 16
Pages: 5173-5183
Peer Reviewed
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