エナンチオセレクティブ・トータル・シンセシス (-) - アルクチニン
Wei Nie1, Jing Gong1, Zhihao Chen1
1Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy , Sichuan University , Chengdu 610041 , P.R. China.
Journal of the American Chemical Society
|May 29, 2019
まとめ
研究者達は 複雑なアルカロイドアーキュチニンの 最初の完全な合成を達成しました ディターペノイドアルカロイド合成におけるこの突破は,重要な構造特性を構築するための新しい戦略を伴う.
科学分野:
- 有機化学
- 自然製品合成
- 薬剤化学
背景:
- アルクチニンなどのディテルペノイドアルカロイドは,潜在的な生物学的活動を持つ複雑な自然製品のクラスです.
- これらのアルカロイドの複雑な構造は,総合成に重大な課題をもたらす.
- 過去の合成努力では,アルクチニンの完全な合成を達成できませんでした.
研究 の 目的:
- C20-ディテルペノイドアルカロイドアーキュチニンの最初の完全な合成を達成するために.
- 複雑なアルカロイドの構造を作るための新しい合成戦略を開発する.
- アルクチニンのラセミックとエナティオメリックの両方の純粋な形態を準備する.
主な方法:
- C4四次中心とピロリジンEリングの初期段階の構築
- アシンメトリック結合添加/アルドールカスケードは,近隣四次ステレオセンター (C4とC5) を確立します.
- デカルボキシル化アリレーション,分子内アザ-ワッカーサイクル化,酸化脱オロマ化/分子内ディエルス-アルダーカスケード,ケチル-オレフィンサイクル化.
主要な成果:
- アルクチニンの完全な合成は,ラセミックと非対称の両方で成功しました.
- C4四次中心とピロリジンEリングの効率的な構築.
- C4 と C5 に近隣の全炭素四分型ステレオセンターのステレオ選択的形成.
結論:
- 開発された合成経路は,アルクチニンおよび関連するディターペノイドアルカロイドにアクセスするための堅固なプラットフォームを提供します.
- 主要な構造モチーフの初期段階の建設の戦略的重要性を検証した.
- この研究は複雑な天然製品の合成のための合成ツールボックスを拡張します.
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