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カリシフィリンB型アルカロイド: (-) -ダフロンガミンHと (-) -イソダフロンガミンHの総合成
Cedric L Hugelshofer1, Vignesh Palani1, Richmond Sarpong1
1Department of Chemistry , University of California , Berkeley , California 94720 , United States.
Journal of the American Chemical Society
|May 11, 2019
まとめ
科学 者 たち は,複合 的 な ダフニフィラム アルカロイド (-) - ダフロンガミン H の 完全 合成 を 初めて 達成 し まし た.この 突破 の ため に,その 分子 を 作る 鍵 の 反応 が 用い られ まし た.
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,潜在的な生物学的活動を持つ複雑な自然産物です.
- これらの複雑な分子の総合成は,ステレオ化学的制御と構造的複雑性において重要な課題を提示します.
研究 の 目的:
- ヘクササイクルのダフニフィラムアルカロイド (-) - ダフロンガミンHの最初の完全な合成を達成する.
- 関連するアルカロイド構造に適用できる 堅固な合成戦略を開発する.
- 更に生物学的評価のために アナログにアクセスできるようにする.
主な方法:
- マニッヒ反応の鍵となる複合性を構築するコンバージェント合成戦略が採用された.
- 効率的なサイクリング反応は,コアポリサイクリックフレームワークを構成するために使用されました.
- ダイアステレオセレクティブ性の高い水素化は4つの連続したステレオセンターを確立した.
- パウソン・カンド反応は,ヒドロインデンの基礎構造の構築のために.
- 最終製品形成のためのエンドゲームリドックス操作.
主要な成果:
- マルチグラムの (-) - ダフロンガミンHの最初の完全合成を成功裏に完了しました.
- 隣接する4つのステレオセンターを持つトリサイクルコアの組立.
- 関連アルカロイドである (-) - アイソダフロンガミンHへのアクセス
- デオキシゾカリシフィリンBの報告された構造の修正
結論:
- 開発された合成経路は, (-) - ダフロンガミンHにアクセスするための効率的でスケーラブルな方法を提供します.
- 合成研究は, (-) - ダフロンガミンHの提案された構造を検証し,ダフニフィルムのアルカロイド生物合成の洞察を提供します.
- この研究は,他の複雑なダフニフィラムアルカロイドとその類似体の合成への道を開く.
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