2013 Fiscal Year Final Research Report
Synthesis of Highly Oxidized Quinolizidine via Reduction of Acylpyridinium Cations
| Project/Area Number |
24790010
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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 |
Chemical pharmacy
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| Research Institution | Kyoto University |
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Principal Investigator |
TSUKANO Chihiro 京都大学, 薬学研究科(研究院), 助教 (70524255)
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| Project Period (FY) |
2012-04-01 – 2014-03-31
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| Keywords | 合成化学 / 有機化学 / 天然物 / 全合成 / アルカロイド |
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| Research Abstract |
A new strategy for synthesizing quinolizidine skeletons by reductive cyclization via acylpyridinium cations was developed. Several functional groups were tolerated under mild reaction conditions. The reaction was successfully extended to a one-pot synthesis of a bicyclic compound.
The new method has been applied to the stereoselective construction of the AB rings of the quinolizidine skeleton of sophoramine-type alkaloids with a cis-cis stereochemistry. The key features of this method involve: (i) the construction of the quinolizidine by the reduction of an acylpyridinium cation; and (ii) the late stage introduction of methoxypyridine by sequential Stille coupling and diastereoselective hydrogenation reactions.
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