2022 Fiscal Year Final Research Report
Gold-catalyzed construction of bicyclo[3.3.1] skeletons and their applications.
| Project/Area Number |
20K05517
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Multi-year Fund |
|---|
| Section | 一般 |
|---|
| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
|
|---|
| Research Institution | Showa Pharmaceutical University |
|---|
Principal Investigator |
|
|---|
| Project Period (FY) |
2020-04-01 – 2023-03-31
|
| Keywords | 金触媒 / ビシクロ[3.3.1]ケタール |
|---|
| Outline of Final Research Achievements |
We have found that the bicyclo[3.3.1]ketal skeleton is obtained in high yield by gold-catalyzed reaction in CF3CH2OH solvent from propargylic alcohols having a hydroxyl group at the γ-position and resorcinol as a nucleophile. The use of naringenin as nucleophile, a type of flavanone, in this reaction gave naringenin-modified bicyclo[3.3.1]ketals in high yield, indicating that it is possible to construct the basic skeleton of the biologically active natural products, Diinsininol and Obochalcolactone in one step. The research is now being expanded to the total synthesis of these natural products.
|
| Free Research Field |
化学系薬学
|
| Academic Significance and Societal Importance of the Research Achievements |
γ位に水酸基を有するプロパルギルアルコール類とレゾルシノール類からの連続反応により、複雑な骨格であるビシクロ[3.3.1]ケタールを一挙に構築できた点が、本研究課題の重要な学術的な意義である。今後、本研究成果を用いて、生理活性物質であるDiinsininolやObochalcolactoneの全合成研究へと展開が見込まれる。また本手法により得られたビシクロ[3.3.1]ケタール類を生理活性試験に展開すれば、生理活性の増減・新たな活性の発見・ファーマコフォアに関する情報獲得など、生物・生命領域への影響も非常に大きい。
|
