アフラバゾールと14-ヒドロキシアフラヴィニンの合成
Hailong Li1, Qifeng Chen1, Zhaohong Lu1
1State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
Journal of the American Chemical Society
|December 10, 2016
まとめ
研究者は,アフラバゾールと14-ヒドロキシアフラビニンの複合インドルディテルペノイドの最初の完全な合成を達成しました. 主なステップは,AlI3が促進したプリンスサイクリングと,構造組立のための高度な結合反応でした.
科学分野:
- 有機化学
- 自然製品合成
- 薬剤化学
背景:
- インドール・ディターペノイドは,重要な生物学的活動を持つ複雑な天然製品の一種である.
- アフラバゾールと14-ヒドロキシアフラビニンは,このクラスのステリック的に要求するメンバーであり,合成の課題を提起します.
- これまでの合成は これらの特定の化合物の完全な合成を達成できなかった.
研究 の 目的:
- アフラバゾールと14-ヒドロキシアフラヴィニンの最初の完全合成を達成するために
- ステリカルに阻害されたインドル・ディターペノイドを製造するための新しい合成戦略を開発する.
- 複雑な分子構造の組み立てにおける特定の反応の有用性を探求する.
主な方法:
- コア構造の形成のためにアルミニウム (III) ヨウ化物 (AlI3) 促進されたアルキンプリンスサイクリングを使用した.
- ペンタシブスティュートされたアレン分子を構築するために,電循環-芳香化の配列を使用した.
- ステル・ミギタ結合を適用して,テトラ置換オレフィンを組み立てました.
- ベンジル系とアリル系C−O結合の末期リダクティブ・クラビングを組み込んだ.
主要な成果:
- アフラバゾール (6) と14-ヒドロキシアフラビニン (8) を合成した.
- 複合的なモチーフの構築におけるAlI3促進アルキーンプリンスサイクリングの有効性を実証した.
- 高度に置換されたアロマティックとオレフィン系を組み立てるための効率的なルートが確立されています.
- ターゲットの天然製品を得るための機能的グループ操作の遅い段階を達成しました.
結論:
- アフラバゾールと14-ヒドロキシアフラビニンの最初の完全合成が成功しました.
- 開発された合成戦略は,複雑なインドル・ディターペノイドにアクセスするための堅固なプラットフォームを提供します.
- この研究は,ステリカルに混じった天然製品を作るための合成ツールキットを拡張します.
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