デスエポキシアンフィディノリドNのエナンチオセレクティブ合成
Barry M Trost1, Wen-Ju Bai1, Craig E Stivala1
1Department of Chemistry , Stanford University , Stanford , California 94305-5080 , United States.
Journal of the American Chemical Society
|November 21, 2018
まとめ
研究者は多段階のアプローチを用いてデセポキシアンフィディノリドNを成功裏に合成しました. この研究は,アンフィディノリドNとカルベノリドIが同一の化合物である可能性を示唆し,構造的関係を明確にする.
科学分野:
- 有機化学
- 合成化学
- 自然製品合成
背景:
- アンフィディノリドNは生物学的活性を持つ複雑な海洋産物です.
- 以前の合成の取り組みは,重要な機能群を設置し,保護群を管理する上で課題に直面しました.
研究 の 目的:
- デスエポキシアンフィディノリドNの全合成を達成する.
- ルテニウム触媒によるアルケン-アルキン結合を含む合成戦略の開発と精製.
- アンフィディノリドNとカルベノリドIの構造的同一性を調査する.
主な方法:
- 多世代総合アプローチ
- 断片組成のための分子内ルテニウム触媒アルケン-アルキン (Ru AA) カップリング.
- 効率的な合成のための保護群の戦略的使用.
- エポキシデーションと二酸化を含む後期機能化.
- 構造解明のための計算分析と13C NMRスペクトロスコーピー.
主要な成果:
- デスエポキシアンフィディノリドNを22つの最長線形と合計33のステップで成功して合成した.
- 3つの合成世代にわたるダイヒドロキシレーションの課題とグループ戦略の保護
- Ru AA カップリング反応の効率とスケーラビリティの改善
- 計算方法によるアンフィディノリドN内の水素結合ブリッジの識別
結論:
- デスエポキシアンフィディノリドNの全合成は,収束戦略によって達成された.
- この研究は,合成方法論の進化,特に Ru AA カップリングとグループ管理の保護を強調しています.
- 比較的なNMR分析は,アンフィディノリドNとカルベノリドIが同じ化合物である可能性を示唆しています.
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