| Project/Area Number |
06672129
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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 | Kobe Pharmaceutical University |
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Principal Investigator |
ITO Masayoshi Kobe Pharm.Univ.Professor, 薬学部, 教授 (20068331)
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| Co-Investigator(Kenkyū-buntansha) |
WADA Akimori Kobe Pharm.Univ.Associate Professor, 薬学部, 助教授 (80158683)
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| Project Period (FY) |
1994 – 1995
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| Project Status |
Completed (Fiscal Year 1995)
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| Budget Amount *help |
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1995: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1994: ¥1,000,000 (Direct Cost: ¥1,000,000)
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| Keywords | Tricarbonyliron complex / Z,E-Dienyl methyl ketone / Condensation / E,Z,E-Trienylesters / Stereoselective synthesis / Retinoid / Carotenoid / Z, E-ジエニルメチルケトン / E, Z, E-トリエニルエステル / E,E-ジエニルメチルケトン / 三置換ポリオレフィン / β-イオニリデンアセトアルデヒド |
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| Research Abstract |
The reaction of various Z,E-dienyl methyl ketone tricarbonyliron complex (1) with nucleophiles was investigated. Treatment of 1 with lithiated acetonitrile or lithium enolate of ethyl acetate afforded a single adduct (2), respectively. In the dehydration reaction of 2 with thionyl chloride, it was found that the ratio of E and Z olefins on newly produced double bond in the product was depend upon the substituents on the diene. However, in all cases, E-isomer was obtained predominantly (E : Z=2-6 : 1). The mechanism of this E- selectivity was assumed that the more stable product was produced from the carbocation intermediate derived from E_1 mechanism. Now, application of this methodology to the stereoselective synthesis of 11Z-retinal, chromophore of visual pigment rhodopsin and iodopsin, is in progress.
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