2022 Fiscal Year Final Research Report
Highly selective synthetic methods using asymmetric synsthesis and ring-opening of highly multi-substituted D-A cyclopropanes as key steps.
| Project/Area Number |
18K05120
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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| Research Institution | Shinshu University |
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Principal Investigator |
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| Project Period (FY) |
2018-04-01 – 2023-03-31
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| Keywords | シクロプロパン / 不斉合成 / 有機化学 / 炭素炭素結合切断 / 中心不斉 / 軸不斉 / 生物活性物質 / 抗ウィルス活性 |
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| Outline of Final Research Achievements |
We developed asymmetric synthetic methods for multi-substituted D-A cyclopropanes. We also found center-to-center asymmetric transcription and center-to-axis asymmetric conversion using the synthesized cyclopropanes as key intermediates. Moreover, these reactions revealed the mechanism based on synthetic data. On the other hand, we also achieved asymmetric synthesis of bioactive lignans using the reactions as key steps. Among them, we synthesized both enantiomers of nilanthin. Using the synthesized niranthin enantiomers, we investigated their anti-viral activity against the hepatitis B virus (HBV) and the inluenza virus (IFV). The results indicate that although the anti-HBV activity does not differ significantly between these two enantiomers, the anti-IFV activity of (-)-niranthin is more potent than that of (+)-niranthin. This result may be interpreted in terms of a different recognition of the enantiomeric structure of a bioactive compound among different virus species.
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| Free Research Field |
有機合成化学
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| Academic Significance and Societal Importance of the Research Achievements |
多置換シクロプロパンの不斉合成を見出したことは、立体的混み合いに起因して合成困難となる化合物群の新規合成法の道を拓いた点で、学術的意義を持つ。特にシクロプロパン類は医薬農薬に多く見られる化合物である点で社会的意義を持つ。一方、シクロプロパンのC-C結合切断を伴う反応では、不斉転写および不斉変換は分子上に不斉構築した中心不斉を効率的に最終段階に伝播し、あるいは、中心から軸へ不斉の種類を効率的に変換する点で、分子の不斉資源の効率的な活用法を開発した点で学術的意義は高い。これらの不斉反応を実際に生物活性物質の合成に応用し、不斉環境とウィルス活性の相関を明らかにした知見も学術的かつ社会的意義が高い。
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