2010 Fiscal Year Final Research Report
Development of new synthetic methodology based on Conia-ene type cyclization
| Project/Area Number |
21790019
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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 | Nagasaki University |
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Principal Investigator |
TAKAHASHI Keisuke Nagasaki University, 医歯薬学総合研究科, 助教 (60380854)
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| Project Period (FY) |
2009 – 2010
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| Keywords | Conia-ene / In(OTf)_3 / シナトリン / オームラリド / 全合成 |
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| Research Abstract |
The key intermediate for the synthesis of omuralide was obtained via conia-ene cyclization followed by ozonolysis ,reduction with NaBH4, silylation, and stereoselective reduction of geminal esters.
Synthetic study on cinatrin C1 was investigated starting from 1-benzyl oxy-(S)-but-3-yne-2-ol. O-H insertion by dizazo malonic ester and following Conia-ene reaction gave Key THF ring intermediate. Dihydroxylation followed by lactone formation, stereoselective reduction of geminal ester, DIBAL reduction and Wittig reaction gave crutial crucial intermediate. Formation of lactone ring by oxidation of THF ring is under investigation.
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[Presentation]
Author(s)
江藤康平, 高橋圭介、石原淳、畑山範
Organizer
第51回天然有機化合物討論会
Place of Presentation
名古屋市
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