| Project/Area Number |
61570996
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Toyama Medical & Pharmaceuticl University |
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Principal Investigator |
YAMAZAKI Takao Toyama Medical & Pharmaceutical University,Faculty of Pharmaceutical Sciences, 薬学部, 教授 (00019093)
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| Co-Investigator(Kenkyū-buntansha) |
TAKAHATA Hiroki Toyama Medical & Pharmaceutical University, Faculty of Pharmaceutical Sciences, 薬学部, 助手 (00109109)
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| Project Period (FY) |
1986 – 1987
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| Project Status |
Completed (Fiscal Year 1987)
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| Budget Amount *help |
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1987: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1986: ¥1,400,000 (Direct Cost: ¥1,400,000)
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| Keywords | Thioamid / <gamma>,<delta>-Unsaturated thioimidates / Iodolactamization / Functionalized <delta>-lactams / Biologically active compounds / <delta>,<epsilon>-Unsaturated thioimidates / <delta>-Lactams / 不斉誘起 / チオアミド / γ,δ-不飽和チオイミデート / 立体選択的反応 |
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| Research Abstract |
<gamma>,<delta>-Unsaturated thioimidates underwent regio-, stereo-, and diastereoselective iodine-induced lctamization to afford functionalized <gamma>-lactams, which were transformed into biologically active compuds [formal total synthesis of (-)-detoxinine, (<+->-trans-2-hydroxymethyl-3-hydroxy-pyrrolidine isolated from Castanospermum australe, <delta>-coniceine, the key intermediate of (<+->)-slaframine, and the constituent of fosenopril (angiotensin converting enzyme inhibitor)].
Iodolactamization of <delta>,<epsilon>-unsaturated thioimidates proceeded regioselectively to provide <delta>-lactams. In this study, we found a new homoenolate reagent (<beta>-tributylstanylpropion-secondary-amide).
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