2015 Fiscal Year Final Research Report
Practical Synthesis of Bioactive Natural Products by Organocatalysts
| Project Area | Advanced Molecular Transformations by Organocatalysts |
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| Project/Area Number |
23105012
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| Research Category |
Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
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| Allocation Type | Single-year Grants |
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| Review Section |
Science and Engineering
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| Research Institution | Kitasato University |
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Principal Investigator |
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| Project Period (FY) |
2011-04-01 – 2016-03-31
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| Keywords | 有機触媒 / ピリドン / イソシアニド / 位置選択的アシル化 / インドール / 全合成 |
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| Outline of Final Research Achievements |
We attempted the chemoselective monoacylation of the insectidal and parasiticidal compound, avermectin B2a, which was discovered in our institute, using the organocatalyst developed by Kawabata’s group. Acetylation, using DMAP as a catalyst under Kawabata’s conditions, gave the monoacetate in 63% yields, without chemoselectivity. Application of the organocatalyst instead of DMAP increased 5-chemoselectivity. The reaction condition was effective for other acylation. Interestingly, trihaloacetylation under this condition provided poor chemoselectivity. After screening various organocatalysts, we found the ent-organocatalyst effectively catalyzed the 4”-regioselective monotrihaloacetylation. These results indicate the chemoselectivity of the acylation was controlled by the combination of organocatalyst with acid anhydride.
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| Free Research Field |
有機合成化学
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