エクロニアラクトーンズの保護基なしの,触媒ベースの全合成
Volker Hickmann1, Manuel Alcarazo, Alois Fürstner
1Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany.
Journal of the American Chemical Society
|August 12, 2010
まとめ
この研究では,5つの移行金属触媒反応を用いて,エクロニアラクトンAとBの簡潔で保護グループのない合成を提示しています. 効率的な経路は,重要なキラルセンターを確立し,複雑なオキシリピン構造を構成します.
科学分野:
- 有機化学 オーガニック・ケミストリー
- トータル・シンセシス トータル・シンセシス
- 自然製品合成 自然製品合成
背景:
- エクロニアラクトンAとBは,茶色藻から分離されたオキシリピンです.
- 彼らの複雑な構造は,重要な合成課題を提示します.
- グループフリー戦略の保護は,効率的な合成のために非常に望ましい.
研究 の 目的:
- 光学的に純粋なエクロニアラクトンAとBの簡潔で保護基のない全合成を開発する.
- これらの天然製品の構築における近代的な移行金属触媒の有用性を探求する.
主な方法:
- クイラルセンターの設置のためのロジウム触媒の1,4-添加.
- カーボサイクルの形成のためのルテニウム触媒による環閉オレフィンメタテシス.
- バナジウム触媒によるエポキシデーションとモリブデン触媒による環閉アルキンメタテシス (RCAM) のマクロサイクリング.
主要な成果:
- エクロニアラクトンAとBの13段階のプロテクティンググループフリー合成が達成されました.
- 主なステップには,エナチオセレクティブ添加,RCM,エポキシデーション,RCAMが含まれていました.
- 新しいモリブデンアルキリジネ複合体は,エポキシード開口なしに,挑戦的なマクロサイクライゼーションを効果的に媒介しました.
結論:
- 開発された合成経路は効率的で,移行金属触媒の力を強調しています.
- この研究は,エクロニアラクトンおよび関連するオキシリピンへのアクセスをするための貴重な方法を提供します.
- この研究は,自然製品合成における高度な触媒的方法の成功した応用を示しています.
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