New Development of Synthetic Reactions using Organoselenoboranes and Application to Synthesis of Pharmacologically Active Compounds
| Project/Area Number |
02670959
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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 | Gifu Pharmaceutical University |
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Principal Investigator |
KATAOKA Tadashi Gifu Pharm. Univ. Professor, 薬学部, 教授 (00082975)
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| Co-Investigator(Kenkyū-buntansha) |
YOSHIMATSU Mitsuhiro Gifu Pharm. Univ. Assistant, 薬学部, 助手 (80240349)
IWAMURA Tatsunori Gifu Pharm. Univ. Assistant, 薬学部, 助手 (70184900)
SHIMIZU Hiroshi Gifu Pharm. Univ. Associate Professor, 薬学部, 助教授 (00082983)
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| Project Period (FY) |
1990 – 1991
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| Project Status |
Completed (Fiscal Year 1991)
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| Budget Amount *help |
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1991: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1990: ¥1,400,000 (Direct Cost: ¥1,400,000)
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| Keywords | Organoselenium Compound / Selenoborane / Radical Addition / Radical Cyclization / C-O Bond Cleavage / Cyclic Ether / alpha-Seleno Carbocation / Diselenoacetal / トリス(フェニルセレ)ノボラン / トリス(メチルセレ)ノボラン / メチレンシクロペンタン / ジセレノアセタ-ル / セレニルラジカル / エ-テル結合開裂 / テトラヒドロフラン / ジヒドロピラン |
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| Research Abstract |
(1)Tris(phenylseleno)borane or tris(methylseleno)borane added to the terminal triple bonds and vinyl selenides were formed. This addition reaction was initiated by oxygen and proceeded by the radical process. The reaction mechanism was investigated by ^1H- and ^<11>B-NMR spectroscopy.
(2)This reaction was applied to the cyclization reaction of enynes containing a nitrogen, an oxygign or a sulfur atom. The intramolecular ring closure of the vinyl radical intermediate to the double bond proceeded preferentially via 5-exo mode of cyclization and the nitrogen, oxygen or sulfur-heterocycles were diastereoselectively given. in good yields.
(3)Tris(phenylseleno)borane underwent the C-O bond cleavage of the tetrahydrofuran and tetrahydropyran derivatives in the presence of zinc chloride or tin(IV)chloride to give omega-phenylseleno alcohols in excellent yields.
(4)Treatment of diselenoacetals with a Lewis acid generated the alpha-seleno carbocations. The olefinic alpha-seleno carbocations underwent the endo-selective ring-closure.
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Report
(3 results)
Research Products
(9 results)
