(-) - カリシフィリン N の総合成
Artem Shvartsbart1, Amos B Smith
1Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania , Philadelphia, Pennsylvania 19104, United States.
Journal of the American Chemical Society
|December 11, 2013
まとめ
複合的なダフニフィラム・アルカロイド (-) - カリシフィリンNの全合成が完了しました. この成果は,ステレオセレクティブの分子内ダイエルス・アルダー反応と困難な水素化を含む先進的な合成戦略を使用した.
科学分野:
- 有機化学 オーガニック・ケミストリー
- 自然製品合成 自然製品合成
- 薬用化学 薬用化学について
背景:
- ダフニフィラムのアルカロイドは,潜在的な生物学的活動を持つ複雑な天然製品のクラスです.
- (-) - カリシフィリンNは,このアルカロイドファミリーの構造的に複雑なメンバーです.
- このような複雑な分子への効率的な合成経路の確立は,さらなる調査のために不可欠です.
研究 の 目的:
- 建築的に複雑なダフニフィラムのアルカロイド (-) - カリシフィリン N.の最初の完全な合成を達成するために.
- 複雑な天然製品合成に適用できる新しい合成方法論を開発し,展示する.
主な方法:
- 合成は,ダイエチラアルミニウム塩化物 (Et2AlCl) によって促進される基板制御の分子内ディエルス・アルダー反応を用いた.
- 主なステップは,環状エノラートアルキル化とスティルカルボニル化,その後ナザロフサイクル化でした.
- 完全に置換された結合ダイエネエステルのディアステロセレクティブ水素化は,重大な,高リスクのステップでした.
主要な成果:
- (-) - カリシフィリンNの全合成が成功しました.
- 合成経路は,重要な変換において高いステレオ選択性を示した.
- この研究は,アルカロイドの複雑なポリサイクルコアを構成する可能性を強調しています.
結論:
- (-) - カリシフィリンNの全合成は,この複雑な天然製品への貴重な経路を提供します.
- 開発された合成戦略は,他のダフニフィラム・アルカロイドの合成にも適用できます.
- この研究は,有機合成と天然製品化学の分野に寄与しています.
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