Development of a method for the preparation of optically active tetrasubstituted allenes via dynamic kinetic resolution: its application to syntheses of natural products
| Project/Area Number |
15K07864
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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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| Research Field |
Chemical pharmacy
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| Research Institution | University of Shizuoka |
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Principal Investigator |
Egi Masahiro 静岡県立大学, 食品栄養科学部, 教授 (80363901)
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| Co-Investigator(Kenkyū-buntansha) |
菅 敏幸 静岡県立大学, 薬学部, 教授 (10221904)
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| Project Period (FY) |
2015-04-01 – 2018-03-31
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| Project Status |
Completed (Fiscal Year 2017)
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| Budget Amount *help |
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
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| Keywords | アレン / 天然物合成 / 有機合成化学 / プロパルギルアルコール / シグマトロピー転位 / 分子内環化 / インデン / 触媒 / イナミド / 天然物 / 全合成 / 選択的還元 / 動的光学分割 |
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| Outline of Final Research Achievements |
Our efficient synthesis of tetrasubstituted allenes was applied to total synthetic studies on natural products. In the synthesis of raputindole A, the allene obtained underwent the intramolecular cyclization to give the tricyclic skeleton. Chelation-controlled reduction was carried out, followed by the introduction of side chains to access raputindole A. Moreover, tetrasubstituted allene was synthesized as a key intermediate toward the total synthesis of taiwaniaquinol D.
In order to develop a synthesis of optically active tetrasubstituted allenes using dynamic kinetic resolution, a racemization catalyst of propargyl alcohols and a chiral silver catalyst that catalyzes sigmatropic rearrangement were investigated.
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Report
(4 results)
Research Products
(2 results)
