Exploitation of high functional chiral building blocks by meso-asymmetrization using Ru^<II> catalyst.
| Project/Area Number |
10671982
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Tohoku University |
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Principal Investigator |
SUGAHARA Tsutomu Tohoku University, Graduate School of Pharmaceutical Sciences, Research Instructor, 大学院・薬学研究科, 助手 (50006350)
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| Project Period (FY) |
1998 – 2000
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| Project Status |
Completed (Fiscal Year 2000)
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| Budget Amount *help |
¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 2000: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1999: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1998: ¥2,000,000 (Direct Cost: ¥2,000,000)
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| Keywords | Ruthenium-chiral amine complex / Chiral building blocks / Asymmetric hydrogen transfer reaction / Chiral cyclopentadienone / Enantioselective synthesis / (+)-Curcuphenol / (+)-Pentenomycin I / (+)-Arnicenone / ルテニウム-キラルアミン錯体 / Baylis-Hillmann反応 / Eschenmoser-Claisen転移反応 / Pauson-Khand反応 / ジアステレオ制御合成 / 不斉分割 / キラルシクロペンタジエノン / 抗生物質 / ペンテノマイシン / シクロペンタジエノン等価素子 / (+) -curcuphenol / (-) -pentenomycin |
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| Research Abstract |
In this research project, the auther applied the catalytic asymmetric hydrogen transfer reaction using Ruthenium-chiral amine complex to obtain chiral KDP and its derivatives.
First, the auther tried the catalytic asymmetric hydrogen transfer reaction of racemic endo-allyl alcohol.
The catalytic asymmetric hydrogen transfer reaction proceeds to give enantiomerically enriched alcohols together with generation of achiral ketones.
The reaction, therefore, loses one half of the starting material and the chiral alcohol will be obtained in maximum 50% yield. But in my case, as the substrate has an appropriate structural background, the chiral enone and the chiral alcohol will be obtained. In fact, the chiral allyl alcohol and the chiral enone were obtained in maximum 96% ee and 54% ee, respectively.
As the lipase-mediated kinetic resolution was not useful method for kinetic resolution of the racemic α-substituted endo-allyl alcohols, the catalytic asymmetric hydrogen transfer reaction was tried to give chiral ketones and chiral allyl alcohols. The reaction, actually, provided the chiral enones and the chiral allyl alcohols in good chemical yields and also with high enantiomeric excess to prove the asymmetric hydrogen transfer method to be a practical method for the resolution of KDP derivatives .
The auther utilized the obtained chiral compounds for the synthesis of the biological active natural products, (+)-curcuphenol, (-)-pentenomycin I and (+)- arnicenone.
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Report
(4 results)
Research Products
(13 results)
