| Project/Area Number |
14002001
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| Research Category |
Grant-in-Aid for Specially Promoted Research
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| Allocation Type | Single-year Grants |
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| Review Section |
Chemistry
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| Research Institution | Tohoku University |
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Principal Investigator |
YAMAMOTO Yoshinori Tohoku University, Department of Chemistry, Professor (60029519)
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| Co-Investigator(Kenkyū-buntansha) |
ASAO Naoki Tohoku University, Department of Chemistry, Associate Professor (60241519)
NAKAMURA Itaru Tohoku University, Department of Chemistry, Assistant Professor (00333899)
TIENAN Jin Tohoku University, Department of Chemistry, Assistant Professor (80431493)
KADOTA Isao Okayama University, Department of Chemistry, Professor (30250666)
PATIL Nitin T. 東北大学, 大学院・理学研究科, 助手 (60400222)
BAJRACHARYA Gan B. 東北大学, 大学院・理学研究科, 助手 (40374904)
上條 真 東北大学, 多元物質科学研究所, 助手
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| Project Period (FY) |
2002 – 2006
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| Project Status |
Completed (Fiscal Year 2006)
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| Budget Amount *help |
¥585,000,000 (Direct Cost: ¥450,000,000、Indirect Cost: ¥135,000,000)
Fiscal Year 2006: ¥87,100,000 (Direct Cost: ¥67,000,000、Indirect Cost: ¥20,100,000)
Fiscal Year 2005: ¥85,800,000 (Direct Cost: ¥66,000,000、Indirect Cost: ¥19,800,000)
Fiscal Year 2004: ¥113,100,000 (Direct Cost: ¥87,000,000、Indirect Cost: ¥26,100,000)
Fiscal Year 2003: ¥117,000,000 (Direct Cost: ¥90,000,000、Indirect Cost: ¥27,000,000)
Fiscal Year 2002: ¥182,000,000 (Direct Cost: ¥140,000,000、Indirect Cost: ¥42,000,000)
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| Keywords | Lewis Acid Catalyst / Transition Metal Catalyst / Convergent Process / Bis-π-allylpalladium / Pronuclcophile / Addition Reaction / C-H Bond Activation / Polycyclic Ether / 芳香環化 / メチレンアジリジン / 分子内反応 / 不斉合成 / ヘテロ環 / 両機能性触媒 / 縮環芳香族化合物 / インドリチジンアルカロイド / メチレンシクロプロパン / インドール / ピリリウムイオン / ナフタレン / 有機分子触媒 / ポリ環状エーエル / 不斉アリル化 / ビスπ-アリルパラジウム / シアノインドール / パラジウム-アクア錯体 / アルキシ / キレーション / 触媒的アルキル化 / 環状エーテル |
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| Research Abstract |
Stereocontroll via σ-π chelation was achieved by using group 13 Lewis acids. During this study, we found that some palladium (II) species act not only as transition metal catalyst but also as Lewis acid catalyst. Based on this finding, total syntheses of natural products, BCH-2051 and vibsanol, were achieved. Furthermore, antibiotics, (+)-ochromycinoneand (+)-rubiginone B2, were synthesized by using novel Au catalyst.
Asymmetric allylation of imine derivatives was achieved by using optically active bis-π-allylpalladium, and the reaction was applied to the preparation of a synthetic intermediate of DMP-777. As a related reaction, novel synthetic method for cyanoindoles via three component coupling was developed. We found that the intramolecular reaction of amines and alkynes give nitrogen heterocycles in the presence of palladium/acetic acid catalyst. This reaction was applied to the total synthesis of an alkaloid, 209D.
α-Allylation of hetero-aromatics and ketones were achieved by using methylenecyclopropane and palladium catalyst. On the other hand, the reaction with methyleneaziridine provided pyrrole derivatives having a pyridine or benzene ring.
Total syntheses of marine polycyclic ethers, gambierol and brevetoxin B, were achieved via the intramolecular allylation followed by ring-closing metathesis.
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