アトロプルランの13段階の総合合成
Shengling Xie1, Gui Chen1, Hao Yan1
1Department of Chemistry and Shenzhen Grubbs Institute , Southern University of Science and Technology , Shenzhen , Guangdong 518055 , China.
Journal of the American Chemical Society
|February 14, 2019
まとめ
アトロパルプーランを 簡潔に合成しました これは自然界では知られていなかった 複合ペンタサイクリック・ディテルペンです この画期的な発見は 骨格の急速な形成に 新しい反応を用いて 関連する自然産物合成の道を開いたのです
科学分野:
- 有機化学
- 自然製品合成
- 合成方法論
背景:
- アトロパープーランは,前例のないテトラサイクロ[5.3.3.04,9 .04,12]-トライデカンの骨格を特徴とするユニークなペンタサイクリック・ディテルペンである.
- アトロパルプランのような複雑な天然製品の合成は,ステレオ化学と骨格構造において重要な課題を提示します.
研究 の 目的:
- アトロパルプランの簡潔で効率的な全合成を開発する.
- 複雑なポリサイクリック・テルペン・フレームワークの構築のための新しい合成戦略を確立する.
主な方法:
- 13段階の合成経路は,初期段階の骨格形成と後期段階の機能化で設計されました.
- 主要な変換は,スパイロサイクル構築のためのリング閉鎖型エニンメタテシスと,エスカフォード組立のための二重酸化脱オロマチゼーション/内分子ダイエルス-アルダーカスケードを含んでいた.
主要な成果:
- アトロパルプランの完全合成が成功し,効率的であった.
- 合成は,保護グループ (PG) の最小限の使用で,全体的に高い効率を示した.
- 新しいテトラサイクロ[5.3.3.04,9.04,12]-トライデカンの骨格が構築されました.
結論:
- 開発された合成アプローチは,アトロパルプランへの実行可能な経路を提供します.
- この方法論は,関連する複雑なディターペンとディターペノイドアルカロイドの将来の合成にインスパイアすることができます.
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