(-) オリドニンの総合成:中断されたナザロフアプローチ
Lingran Kong1, Fan Su1, Hang Yu1
1Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.
Journal of the American Chemical Society
|December 6, 2019
まとめ
この研究は,中断されたナザロフ反応を用いた (-) - オリドニンの最初のエナンチオセレクティブ・トータル合成を示しています. この新しいアプローチは,難しい四次炭素を含む複雑な四次循環構造を成功裏に構築した.
科学分野:
- 有機化学
- 合成化学
- 自然製品合成
背景:
- (-) - オリドニンは,潜在的な生物学的活動を持つ高度に酸化したエンタカウラノイドです.
- (-) オリドニンの複雑な構造は,特に複数のステレオセンターと四次炭素の存在により,重要な合成課題を提示する.
研究 の 目的:
- (-) オリドニンの最初のエナンチオセレクティブ・トータル合成を達成する.
- テトラサイクルコアを構成するために中断されたナザロフ反応を用いた新しい合成戦略を開発する.
主な方法:
- エナチオセレクティブ・トータル合成
- ナザロフ反応を中断した
- ナザロフ/ホソミ・サクライ・カスケード
- リング再配置反応
- 末期リドックス操作
主要な成果:
- (-) オリドニンのテトラサイクル構造の成功
- 挑戦的な四次炭素の形成を含むステレオ化学の制御.
- 高度酸化したエンタカウラノイド構造の新合成.
結論:
- 開発された合成経路は, (-) - オリドニンへの効率的でエナンチオセレクティブなアクセスを提供します.
- この研究は,複雑な分子合成における中断されたナザロフ反応の有用性を強調しています.
- この研究は,オリドニン誘導体とその生物学的性質のさらなる探求のための舞台を設定します.
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