アルクチニジン,アルクチニン,アルクチニンの非対称的全合成
Shupeng Zhou1, Kaifu Xia1, Xuebing Leng2
1State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences , Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.
Journal of the American Chemical Society
|July 6, 2019
まとめ
研究者は3つのC20-ディテルペノイドアルカロイド:アルクチニジン,アルクチニン,およびアルクチンの非対称的な総合成を達成しました. 主なステップは,ダイエルス-アルダー反応とプリンス循環/ワグナー-ミールウェイン再配置カスケードで,コア構造を構成した.
科学分野:
- 有機化学
- 自然製品合成
- アルカロイド化学
背景:
- ディテルペノイドアルカロイドは,多様な生物学的活動を持つ重要な自然製品のクラスです.
- C20-ディテルペノイド骨格を特徴とするアルカロイドは,複雑な合成課題を提示する.
- これらの複雑な分子の立体化学を理解することは,構造-活動関係の研究に不可欠です.
研究 の 目的:
- アルクチニジン,アルクチニン,アルクチニンの最初の非対称的全合成を達成するために.
- これらのアルカロイドのペンタサイクリックコアを構成するための効率的な合成戦略を開発する.
- 主要なステレオセンターの絶対的な構成を確認するために,特にアーキュチンで.
主な方法:
- ペンタサイクルの中間物質の迅速な組み立てのために2つのディエルス-アルダー反応を使用した.
- プリンス・サイクライゼーションとワグナー・ミールウェイン再配列を用いたカスケード配列を開発し,アルクチニジン・コアを構築した.
- ピロリンモチーフの構築のために,化学選択的還元性アミネーションと自発的なイミン形成を使用した.
主要な成果:
- アルクチニジン,アルクチニン,アルクチニンを 合成した.
- 酸素化されたペンタサイクリック中間物質のスケーラブルな経路を確立した.
- 合成とX線結晶学により,アキュチンのα-炭素の (S) 構成を確認した.
結論:
- 開発された合成戦略は,アルキュチン型アルカロイドへの効率的なアクセスを提供します.
- 合成は,複雑なペンタサイクルのディターペノイドアルカロイドの構造を構築するための重要なステップを検証します.
- アルクチンのステレオ化学的配分は決定的に確立されています.
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