連続インドール機能化を用いたペンタサイクリック (-) - アンビギンPの総合成
Rebecca E Johnson1, Hwisoo Ree1, Marco Hartmann1
1Department of Chemistry , University of California , Berkeley , California 94720 , United States.
Journal of the American Chemical Society
|February 1, 2019
まとめ
研究者らは,ペンタサイクリックアンビギュインPの最初の合成を報告した.この新しい化学合成は,インドルコアの連続アルキル化を使用し,複雑な自然製品フレームワークの迅速な構築を可能にします.
科学分野:
- 有機化学
- 自然製品合成
- 薬剤化学
背景:
- アンビギンは複雑なペンタサイクルの構造を持つ自然製品のクラスです.
- 曖昧な生物の生物学的活動は,さらなる研究のために効率的な合成経路を必要とします.
- これまでの合成は,曖昧なPのペンタサイクリックコアを達成できなかった.
研究 の 目的:
- ペンタサイクルのアンビギュイン,特にアンビギュインPの最初の完全合成を報告する.
- コアペンタサイクルフレームワークの迅速な構築を可能にする合成戦略を開発する.
- 関連する曖昧な同類体の合成の可能性を備えた多機能な中間物質を製造する.
主な方法:
- インドール核の連続アルキル化
- C2アルキル化のためのニコラス反応の適用で7つの環を形成する.
- C12でアミド指向機能化して 四次中心を確立する.
主要な成果:
- ペンタサイクリックアンビギュインPの 合成が成功しました
- ニコラス反応による特徴的な溶融7つ環の効率的な構築.
- アミド指向機能化を用いたキー四次中心の形成.
- 汎用性の高い後期的な中間物質の生成
結論:
- 開発された合成戦略は,ペンタサイクルの曖昧性にアクセスするための堅固な方法を提供します.
- この合成は,ニコラス反応と複雑な分子組成におけるアミド誘導機能化の有用性を強調している.
- 遅い段階の中間物質は,他のペンタサイクルの曖昧な天然製品を合成する可能性を秘めています.
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