Synthesis of Biologically Active Bislactone Utilizing an Indium-mediated Reformatsky-Claisen Rearrangement and Development of Chiral Claisen Rearrangement
Project/Area Number |
24590011
|
Research Category |
Grant-in-Aid for Scientific Research (C)
|
Allocation Type | Multi-year Fund |
Section | 一般 |
Research Field |
Chemical pharmacy
|
Research Institution | Nagasaki University |
Principal Investigator |
ISHIHARA Jun 長崎大学, 医歯薬学総合研究科(薬学系), 准教授 (80250413)
|
Project Period (FY) |
2012-04-01 – 2015-03-31
|
Project Status |
Completed (Fiscal Year 2014)
|
Budget Amount *help |
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
|
Keywords | 有機合成 / 天然物合成 / 転位反応 / クライゼン転位反応 / 不斉合成 / ジヒドロスピロスリオリド |
Outline of Final Research Achievements |
The asymmetric synthesis of (-)-dihydrosporothriolide, a biologically active bis-γ-butyrolactone, was achieved. The synthesis includes a D-proline-catalyzed asymmetric aminooxylation, indium-mediated Reformatsky-Claisen rearrangement of an α,α-dibromoacetate derivative, and diastereoselective dihydroxylation. The route requires no protective group manipulation and allows the concise seven-step synthesis of (-)-dihydrosporothriolide from n-octanal. The synthesis illustrates the synthetic utility of our indium-mediated Reformatsky-Claisen rearrangement applicable to base-sensitive substrates.
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Report
(4 results)
Research Products
(18 results)