セプテディンと7-デオキシセプテディンの総合成
Shupeng Zhou1, Rui Guo1, Peng Yang1
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
|June 7, 2018
まとめ
この研究は,複合体C20-ディテルペノイドアルカロイドセプテディンとそのアナログの最初の非対称的全合成を示しています. 主なステップは,エナチオセレクティブポリエンのサイクリングと異常なディエルス-アルダー反応でした.
科学分野:
- 有機化学
- 総合成
- 自然製品 化学
背景:
- セプテディンは,独特の酸素化されたヘプタサイクルの構造を持つ複雑なC20-ディテルペノイドアルカロイドである.
- セプテディンの複雑な構造は,重要な合成課題を提示します.
研究 の 目的:
- セプテディンの最初の非対称的全合成を達成するために (2).
- セプテディンの7デオキシアナログを合成する (3).
主な方法:
- エナチオピュアトリサイクル中間体のためのカレラポリエネサイクリング.
- ビサイクロ[2.2.2]オクタンの核構造のためのアニオンダイエルス-アルダー反応.
- α-メチルケトン装置のためのイリジウム触媒のアリルアルコールイソメリゼーション.
- 二次ヒドロキシル群の導入のためのサンフォードCsp3-H酸化.
- オクサゾリジノピペリジンの最終組成のための還元性アミネーションとN,O-ケタリゼーション.
主要な成果:
- セプテジン (2) とその7デオキシアナログ (3) の非対称的全合成が成功しました.
- ポリエンのサイクル化,ディエルス・アルダー反応,C−H酸化を含む重要な合成変換の実証.
- 複雑なヘプタサイクルの構造で ステレオケミカル制御が可能です
結論:
- 開発された合成経路は,セプテジンとその類似体にアクセスを提供します.
- この作品では 複雑な自然製品構造を 構築するための革新的な戦略を紹介しています
- この方法論は,関連するディターペノイドアルカロイドの合成に適用できる.
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