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新しく,高度に対称的なビス・オクサ・ブリッジされた化合物の合成
Faiz Ahmed Khan1, Jyotirmayee Dash
1Department of Chemistry, Indian Institute of Technology, Kanpur-208 016, India.
Journal of the American Chemical Society
|March 14, 2002
まとめ
新型ペンタサイクルのビス・オクサ・ブリッジ化合物は,容易に入手可能な出発材料を使用して効率的に合成されました. この3段階の方法は,ストレートオキサブリッジドリバティブへの多用途な経路を提供します.
科学分野:
- 有機化学 オーガニック・ケミストリー
- 合成化学 合成化学とは
- 薬用化学 薬用化学について
背景:
- bis-oxa-bridged構造を持つ新型ペンタサイクリック化合物は,有機合成において興味を惹きます.
- 複雑なポリサイクル分子への効率的な合成経路は,非常に求められています.
研究 の 目的:
- 新型ペンタサイクリックバイオキシブリッジ化合物の効率的な3段階合成を開発する.
- 関連するストレインオックスブリッジドリバティブを合成するための開発された方法の汎用性を実証する.
主な方法:
- 合成はテトラクロロ-5,5-ジメトキシcyclopentadieneと1,4-cyclohexadieneから開始されました.
- 2:1バイアドクトのルテニウム触媒による酸化に続いて,1ポット変換.
- エステル化により,最終的なペンタサイクルのビス・オクサ・ブリッジ化合物が得られます.
主要な成果:
- 新しいペンタサイクルのビス・オクサ・ブリッジ化合物 (化合物8) が驚くべき効率で合成されました.
- 3段階合成の総収量は29.1%でした.
- この方法は,他のノルボニルアルファディケトンにも成功裏に適用され,相応のストレントオクサブリッジドリバティブが得られました.
結論:
- 新型ペンタサイクルのビス・オクサ・ブリッジ化合物のシンプルで効率的な3段階の合成戦略が確立されています.
- 開発された方法は,ストレントオキサブリッジ分子構造にアクセスするための汎用的なアプローチを提供します.
- この研究は,ポリサイクル化合物合成の分野に貴重な貢献をもたらします.
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Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
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