2011 Fiscal Year Final Research Report
Synthetic Study of Brasilicardin A, a novel immunosuppressive agent
| Project/Area Number |
22710206
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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 |
Living organism molecular science
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| Research Institution | Hokkaido University |
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Principal Investigator |
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| Project Period (FY) |
2010 – 2011
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| Keywords | ブラシリカルジン / 全合成 / S_N2'反応 / 四級不斉炭素 / α-シアノカルバニオン / 共役付加反応 / パーヒドロフェナントレン |
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| Research Abstract |
This research mainly aimed at chemical synthesis of Brasilicardin A, a novel immunosuppressive agent of broad interest. As a result, we developed(i) a new and practical method for stereoselective construction of an all-carbon quaternary stereogenic center on a carbocyclic ring based on regio-and stereoselective S_N2' alkylation reactions ofγ,δ-epoxy-α,β-unsaturated cyclic ketones, and(ii) a stereoselective method for constructing the anti-syn-anti-perhydrophenanthrene skeleton(ABC ring system) of Brasilicardin A, which represents one of the largest obstacles to the total synthesis.
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