触媒性ヒドロキシクロプロパノール環開きカルボニラティブ・ラクトニゼーション
Xinpei Cai1, Weida Liang1, Mingxin Liu1
1Department of Chemistry and Center for Cancer Research, Purdue University, West Lafayette, Indiana 47907, United States.
Journal of the American Chemical Society
|July 21, 2020
まとめ
パラジアム触媒による新しい反応は,ヒドロキシクロプロパノールからバイサイクルラクトンを効率的に生成します. この方法は自然製品の合成を含む温和な条件と広範なアプリケーションを提供します.
科学分野:
- 有機化学
- カタリシス
- 合成方法論
背景:
- バイサイクルのG-ラクトンは,多くの天然製品における重要な構造モチーフである.
- これらの特権的な骨組みへの 効率的な合成経路は 医薬品化学において非常に求められています
- 既存の方法はしばしば厳しい条件を必要とし,広く適用できない.
研究 の 目的:
- テトラヒドロフーラン (THF) やテトラヒドロピラン (THP) で融合したバイサイクル γ-ラクトンを合成するための新しいパラジウム触媒方法の開発.
- 複雑なラクトン構造にアクセスするための多用途でスケーラブルな炭素化戦略を確立する.
- 自然製品の合成におけるこの方法の有用性を実証する.
主な方法:
- ハイドロキシクロプロパノールのパラジウム触媒リング開きカルボニラティブラクトニゼーション.
- 反応条件の最適化,触媒,リガンド,溶媒,温度など
- 開発された方法を自然製品の総合成に適用する.
主要な成果:
- 様々なTHFとTHPを融合させたバイサイクル γ- ラクトンの効率的な合成が達成された.
- 反応は軽度な条件下で進行し,機能群の耐性が良好である.
- この方法は (±) - パエオニリドの簡潔な全合成に成功しました.
- 合成されたラクトンは,さらなる多様化のための多用途な中間物質として機能する.
結論:
- パラジウム触媒による新しい効率的な炭酸乳酸化が開発された.
- この方法は,温和でスケーラブルな条件下で貴重なバイサイクリック γ-ラクトン・スキャファードにアクセスできます.
- 合成戦略は天然製品の合成に適用され,他の医学的に重要な構造に容易に多様化することができます.
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