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Updated: Jul 15, 2026
09:45
Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
(-) ギャランタミンと (-) モルヒンの異なったエナンチオセレクティブ合成
Barry M Trost1, Weiping Tang, F Dean Toste
1Department of Chemistry, Stanford University, Stanford, California 94305, USA. bmtrost@stanford.edu
Journal of the American Chemical Society
|October 20, 2005
まとめ
新しい合成戦略により,ガランタミンやモルヒンのようなオピエットとアマリルリダセアアルカロイドを効率的に生成します. この方法では,パラジウム触媒による非対称性アリルアルキレーション (AAA) および他の重要な反応を使用して,簡素化された合成を行います.
科学分野:
- 有機化学 オーガニック・ケミストリー
- 合成化学 合成化学とは
- 薬用化学 薬用化学について
背景:
- オピエットとアマリルリダセア亜kaloidsは,多様な生物学的活動を持つ重要な天然製品です.
- これらのアルカロイドへの既存の合成経路は,長引く可能性があり,効率性が欠けている.
- これらの貴重な化合物にアクセスするために,新しい,収束した合成戦略の開発は極めて重要です.
研究 の 目的:
- オピエットとアマリルリダセアのアルカロイドのための効率的で異なる合成戦略を開発する.
- ガランタミンおよび関連する構造物の立体選択合成を確立する.
- これらのアルカロイドクラスのコア骨格の構築のための新しい反応を探求する.
主な方法:
- パラジウム触媒による非対称性アリルアルキレーション (AAA) によって,主要なステレオセンターを確立する.
- 環形成のための分子内ヘック反応.
- ヘックビニレーションと可視光誘発型ヒドロアミネーションは,複雑なポリサイクルシステムを構築するために用いられる.
主要な成果:
- 簡単に入手可能な原料から,ピボタルトライサイクリック中間物質の6段階の合成.
- 中間物質を (-) - ガランタミンに効率的に2つのステップで変換する.
- コデイン/モルヒンの骨格の第4輪をヘックビニレーションで成功裏に構築した.
- コデインへの最終的なリング閉鎖とモルヒンへの後の変換のための新しい可視光促進水素アミネーション.
結論:
- 開発された戦略は,ギャランタミン,コデイン,モルヒンへの効率的で汎用的な経路を提供します.
- パラジウムで触媒化されたAAAの使用は,合成の初期にステレオ化学を制御するために不可欠です.
- 採用された反応は,複雑なアルカロイドの合成のための強力なツールキットを提供します.
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