ダポルハミンBとダポルハミンBラクトンの総合合成
Lian-Dong Guo1, Jieping Hou1, Wentong Tu1
1Department of Chemistry and Shenzhen Grubbs Institute , Southern University of Science and Technology , Shenzhen , China.
Journal of the American Chemical Society
|July 13, 2019
まとめ
研究者らは,複合的なダフニフィラム・アルカリド・ダポルハミンBの最初のエナチオセレクティブ・総合成を達成した. この突破は アザ・アダマンタン天然製品への 新しい合成経路を提供します
科学分野:
- 有機化学
- 自然製品合成
- 薬剤化学
背景:
- ダフニフィラムのアルカロイドは,構造的に複雑で,重要な生物活性性で知られている.
- ダポルハミンBのユニークなアザ・アダマンタン・コアと複数のステレオセンターは,かなりの合成課題を提示しています.
研究 の 目的:
- 自然産物ダポルダミンBの最初の 選択的合成を報告する.
- アザ・アダマンタン天然製品の 簡潔で効率的な合成戦略を開発する.
主な方法:
- マニッヒ反応を 重要なステップとして利用した.
- α-ブロモ-α,β-不飽和ケトンの最適化合成を用いた.
- サブストラットに依存した内分子アザ-マイケルの添加とアミドの活性化による無効化
主要な成果:
- ダポルハミンBとラクトンの誘導体を 選択的に合成しました
- 3つの完全に置換されたものを含む8つの隣接するステレオセンターを特徴とする簡潔な合成ルートを確立しました.
- SN2'-型乳酸化とホーナー・ワドズワース・エモンズ・オレフィネーションを含む重要な変換が実証されている.
結論:
- 開発された合成アプローチは,アザ-アダマンタン天然製品の最初の完全な合成を表しています.
- この研究は,複雑なアルカロイド構造にアクセスするための貴重な方法論を提供します.
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