Short total synthesis of prostaglandin
| Project/Area Number |
25620074
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Synthetic chemistry
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| Research Institution | Tohoku University |
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Principal Investigator |
Hayashi Yujiro 東北大学, 理学(系)研究科(研究院), 教授 (00198863)
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| Project Period (FY) |
2013-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | 有機触媒 / 全合成 / 不斉触媒 / プロスタグランジン / 有機合成 / 不斉合成 / 天然物合成 |
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| Outline of Final Research Achievements |
Prostaglandins regulate a broad range of physiological activities and some of their derivatives are used as effective drugs, but previously their preparation has required many operations. In the present investigation, we developed formal 3+2 cycloaddition reaction, which proceeds between succinaldehyde and nitroalkene catalyzed by diphenylprolinol silyl ether, which has been developed in my group, to afford substituted cyclopentanecarbaldehyde with excellent diastereo- and enantioselectivity. Using this reaction as a ley step, we established one of the shortest and highest-yielding asymmetric total syntheses of prostaglandin A1 and E1 methyl ester in a small number of synthetic operations using only three pots via an environmentally-benign process. Newly-developed organocatalysis technology and practical, single-pot operations involving several successive reactions produce PGA1 and PGE1 efficiently.
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Report
(4 results)
Research Products
(12 results)
