| Project/Area Number |
13650913
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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 |
Synthetic chemistry
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| Research Institution | Tokyo Institute of Technology |
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Principal Investigator |
KOBAYASHI Yuichi Tokyo Institute of Technology, Faculty of Bioscience and Biotechnology, Associate Professor, 大学院・生命理工学研究科, 助教授 (90153650)
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| Project Period (FY) |
2001 – 2003
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| Project Status |
Completed (Fiscal Year 2003)
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| Budget Amount *help |
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2003: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2002: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2001: ¥1,300,000 (Direct Cost: ¥1,300,000)
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| Keywords | cyclopentene-1,3-diol / Grrignard Reagent / Organocopper / S_N2 / anti S_N2' / 12-oxo-PDA / OPC:8-0 / Δ^<12>-PGJ_2 / 4-シクロペンテン-1,3-ジオール / Grignard試薬 / 銅触媒 / シクロペンタノイド / 12-oxo-PDAの合成 / OPC-8:0 / エピジャスモン酸 / PPARγアゴニスト / シクロペンタノイドム / Δ^<13>-PGJ_2 / シンクロペンテン-1, 3-ジオール / 炭素原子団の導入 / CH_2OHの導入 / CuCN / シンクロペンタノイド |
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| Research Abstract |
4-Cyclopentene-1,3-diol monoacetate (1) is an attractive compound for synthesis of cyclopentanoids. However, the use along this line had been limited due to lack of efficient reactions for installation of carbon nucleophiles onto the ring. Herein, we have developed new reactions based on RMgX and Cu(I) for S_N2 and anti S_N2' reactions, thus producing 4-substituted 2-cyclopenten-1-ols (1,4-isomers) or 2-substituted 3-cyclopenten-1-ols (1,2-isomers) depending on the ratio of RMgZ/Cu(I) and solvent used. In addition, we developed reagents and conditions for attaching second carbon nucleophiles to the 1,4-isomers produced above. We applied these reactions to synthesis of 12-oxo-PDA, OPC-8:0, OPC-8:0, and Δ^<12>-PGJ_2.
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