| Project/Area Number |
12304042
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| Research Category |
Grant-in-Aid for Scientific Research (A)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
物質変換
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| Research Institution | Hokkaido University |
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Principal Investigator |
MIYASHITA Masaaki Hokkaido University, Hokkaido Unive., Grad. School of Sci., Prof. (50006326)
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| Co-Investigator(Kenkyū-buntansha) |
TANINO Keiji Hokkaido Univ., Grad. School of Sci., Asso. Prof. (40217146)
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| Project Period (FY) |
2000 – 2002
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| Project Status |
Completed (Fiscal Year 2002)
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| Budget Amount *help |
¥21,030,000 (Direct Cost: ¥18,300,000、Indirect Cost: ¥2,730,000)
Fiscal Year 2002: ¥5,850,000 (Direct Cost: ¥4,500,000、Indirect Cost: ¥1,350,000)
Fiscal Year 2001: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Fiscal Year 2000: ¥9,200,000 (Direct Cost: ¥9,200,000)
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| Keywords | epoxy alcohol / natural product synthesis / acyclic organic molecules / Ingenol / Scytophycin C / epoxide-opening reaction / Zincophorin / stereospecific acyclic stereocontrol / エポキシドの立体特異的相互変換 / アセチレンジコバルト錯体 / 付加環化反応 / 不斉全合成 / 立体特異的鎖状有機分子構築法 / 二重立体反転 / 立体特異的 / C-2位選択的置換反応 / エポキシスルフィド / 全合成 / 立体特異的相互変換 / ミサキノライド / サイトフィシン |
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| Research Abstract |
Development of highly stereoselective synthetic methodologies for acyclic organic molecules having contiguous asymmetric centers is one of the important research projects in modern synthetic organic chemistry in context with the chiral synthesis of biologically and medicinally important compounds. This research project was carried out aiming at the development of highly stereoselective synthetic methodologies for acyclic organic molecules having contiguous asymmetric centers using stereospecific substitution reactions of epoxides as synthetic strategy .
when this grant was provided.
(1) The C2 selective alkyl and alkynyl substitution reactions of 2,3-epoxy alcohols by the use of organoaluminum ate complexes.
(2) Novel and powerful reagent system for stereospecific alkylation-silylation reactions of epoxides.
(3) A regio- and stereoselective a-methylation of γ, δ-epoxy-α, β-unsaturated esters with a Me_2Zn-CuCN reagent.
(4) Stereospecific acyclic stereocontrol with double inversion of the configuration.
(5) The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates.
(6) Stereoselective total synthesis of PM Toxin A, a corn Host-Specific Pathotoxins.
(7) Total Synthesis of Ingenol.
(8) Stereoselective total synthesis of zincophorin, the unique ionophore antibiotic.
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