ハイブリダフニフィリンBの総合成
Wenhao Zhang1, Ming Ding1, Jian Li1
1State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.
Journal of the American Chemical Society
|March 2, 2018
まとめ
研究者らは,複合的なダフニフィリンアルカロイドであるハイブリダフニフィリンBの最初の完全な合成を達成しました. この突破は,合成有機化学を進めるために,後期的な分子間ダイエルス-アルダー反応を利用した.
科学分野:
- 有機化学
- 自然製品合成
- 薬剤化学
背景:
- ハイブリダフニフィリンBは11のリングと19のステレオセンターを持つ複雑なダフニフィリンアルカロイドです.
- ハイブリダフニフィリンBの複雑な構造は,総合成に重大な課題を提示しています.
研究 の 目的:
- ハイブリダフニフィリンBの 最初の完全合成を報告する
- ダフニロンゲラニンBを含む主要な中間物質のスケーラブルな経路の開発
- 遅い段階の分子間ダイエルス-アルダー反応などの新合成戦略を探求する.
主な方法:
- ダフニロンゲランBへのスケーラブルな経路が確立された.
- 望ましくないコップの再編成を抑制するために最適化された.
- 合成には,サイクロペンタディエンとアスペルロシドテトラアセテート誘導体との間の遅い段階の分子間ダイエルス-アルダー反応が含まれています.
- ディエンの形成とディエルス・アルダー反応のための1ポットプロトコルが開発された.
主要な成果:
- ハイブリダフィリンBの最初の完全合成が成功しました.
- ダフニウニンEとデヒドロダフニロンゲラニンBも合成された.
- 合成は,複雑なアルカロイドの枠組みを構築する際の遅い段階の分子間ダイエルス-アルダー反応の有用性を実証した.
- 新しい"ポットプロトコルにより,ダイエンの形成とサイクロアディションのプロセスを簡素化しました.
結論:
- ハイブリダフニフィリンBの総合成は,天然製品合成の分野に貴重な貢献を提供します.
- 開発された合成戦略は,他の複雑なダフニフィラムアルカロイドにアクセスする可能性を秘めています.
- この研究は,複雑な分子構造を組み立てるためのダイエルス-アルダー反応の力を強調しています.
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