2014 Fiscal Year Final Research Report
Total synthesis of spirolide C for elucidation of its potent inhibitory mechanism on acetylcholine receptors
| Project/Area Number |
24710249
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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 |
Living organism molecular science
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| Research Institution | Osaka University |
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Principal Investigator |
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| Project Period (FY) |
2012-04-01 – 2015-03-31
|
| Keywords | スピロリド / スピロアセタール / Diels-Alder反応 / 構造解析 / 化学合成 |
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| Outline of Final Research Achievements |
For total synthesis of spirolide C, the synthesis of two main structures (6,5,5-bisspiroacetal unit and 7,6-spiroimine unit) has been investigated. First, the synthesis of 6,5,5-bisspiroacetal was attempted via the conformationally-restricted spirocyclization using a linker-tethered precursor. Although the key spirocyclization resulted in the selective formation of the undesired isomer, the important knowledge such as how to analyze the structure of products was obtained, which should be informative for future development. Next, for the construction of the 7,6-spiroimine unit, the selective Diels-Alder reaction using 2-silyl-dienyne and alfa-methylene-epsilon-lactam was successfully developed to give the desired exo-cycloadduct with high selectivity.
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| Free Research Field |
天然物化学、合成有機化学
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