環開き機能化によるアルカロイドのバイオパターンの再編成

Hyeonggeun Lim¹, Sikwang Seong¹, Youyoung Kim^1,2

¹Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Korea.

Journal of the American Chemical Society

|November 16, 2021

まとめ

この研究は,自然産物を有価な二次代謝産物に変換することを可能にする,三次アミンの新しいリング開き機能化方法を導入しています. 多様性のある化学戦略は自然を模倣する

科学分野:

有機化学
自然製品合成
化学生物学

背景:

生物合成の経路は自然産物を頻繁に再配置し構造的な多様性を生み出します
自然の再編成戦略を化学的に真似ることで,豊富な自然産物から付加価値の二次代謝産物を得ることができます.
複雑な分子の再編成のための普遍的な化学的方法の開発は,依然として重要な課題です.

研究の目的:

構造的に多様な天然製品の再構成のための多用途で穏やかな化学的方法を開発する.
簡単に手に入る天然製品を,他の付加価値のある二次代謝産物に変換できるようにする.
生物遺伝学的に重要な前駆体の化学反応を刺激された再組織化で探求する.

主な方法:

三次アミンの新種のリング開き機能が報告された.
局所生成の二酸化炭素を二酸化メチル化アンモニアム塩の中間産物として利用する.
安定したアンモニア塩のα位置を攻撃するために外部ヌクレオフィルを使用します.

主要な成果:

シキリネガ,イボガ,サルパギンアルカロイドをネオシキリネガ,チッピイン/ディピニン,ボバシン型ビシンドルアルカロイドに順番に変換することが実証された.
アルカロイド再構成におけるメソッドの有用性と一般性を示した.
生物遺伝学的に重要な前駆体の化学反応を調べました

結論:

開発されたリング開封機能化方法は,天然製品の構造的多様化のための強力なツールを提供します.
このアプローチは自然の再配置に基づく多様化を模倣する化学的戦略を提供します
この方法は,複雑なアルカロイドと関連する構造の合成を容易にする.

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