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
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| Project Status |
Completed (Fiscal Year 2014)
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| Budget Amount *help |
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
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| 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 / スピロイミン / 全合成 / 構造決定 |
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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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Report
(4 results)
Research Products
(8 results)
