| Project/Area Number |
17K08222
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Multi-year Fund |
|---|
| Section | 一般 |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Japan Women's University |
|---|
Principal Investigator |
ABE Hideki 日本女子大学, 理学部, 教授 (00328551)
|
|---|
| Project Period (FY) |
2017-04-01 – 2020-03-31
|
| Project Status |
Completed (Fiscal Year 2019)
|
| Budget Amount *help |
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2019: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
|
|---|
| Keywords | 三環性フムラノライド / wilfolide B / ラジカル環化反応 / 異性化反応 / 閉環メタセシス / 類縁体 / Knoevenagel 縮合 / フムラノライド類 / 全合成 |
|---|
| Outline of Final Research Achievements |
With the aim of studying the structure-activity relationship of humulene-based tricyclic fumulanolides, development of an efficient synthetic method for them. After synthesizing an aldehyde having a Z-unsaturated ester from 2,2-dimethyl-1,3-propanediol as a starting material, the radical cyclization using samarium iodide afforded the bicyclic lactone. Then, two types of side chains were constructed for the bicyclic lactone via introduction of a butenyl group at the lactone carbonyl α position, and an isomerization was performed to adjust the stereochemistry. Finally, the construction of the 8-membered ring by ring closing metathesis followed by catalytic hydrogenation allowed us to achieve the first total synthesis of wilfolide B.
|
| Academic Significance and Societal Importance of the Research Achievements |
今回確立した三環性フムラノライド wilfolide B の全合成経路は、類似した三環性化合物の合成を可能とするため、今後構造活性相関研究への展開を期待させる成果が得られたものと考えている。またそこから生まれる新しい知見は、フムラノライド類の利用価値を判別するための材料の１つになるものと思われることから、今回の成果は非常に意義深い成果であると考えられる。
|
