アイソドモ酸GとHの合成総量
Scott E Denmark1, Jack Hung-Chang Liu, Joseck M Muhuhi
1Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. sdenmark@illinois.edu
Journal of the American Chemical Society
|October 8, 2009
まとめ
海洋天然産物であるイソドモ酸GとHは,新しいシリルカルボサイクリングとシリコンベースのクロスカップリング戦略を使用して合成されました. この効率的な方法は,これらの複雑なカイノイド化合物へのアクセスを提供します.
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 自然製品の合成
- マリン・ケミストリー (海洋化学)
背景:
- イソドモ酸を含むカイノイドの天然製品は,重要な生物学的活性を持っています.
- 複雑な海洋天然製品の総合合成は,合成戦略と実行においてかなりの課題を提示します.
研究 の 目的:
- イソドモ酸GとHの効率的な全合成を記述する.
- シリルカルボサイクリングとシリコンベースのクロスカップリングを含む新しい合成戦略を開発し,適用する.
主な方法:
- 連続シリルカルボサイクリング/シリコンベースのクロスカップリング戦略.
- ロジウム触媒による, (l) -ビニルグリシン由来1,6-エニンの炭化シリルカルボサイクリング.
- 脱塩イオジングとアルケニル-アルケニルシリコンベースのクロスカップリング反応.
主要な成果:
- イソドモ酸Gの12段階合成と,イソドモ酸Hの13段階合成が成功しました.
- 脱塩性ヨウ素化 (逆転または保持) によるヨウ素のステレオ制御導入.
- カイノイド核構造の効率的な構築.
結論:
- 開発された合成経路は,同位体酸GとHへの効率的なアクセスを提供します.
- ヨドデシリレーションのメカニズム的な理解は,立体化学的制御を可能にしました.
- この戦略は,他の複雑なカイノイド構造の合成にも適用できます.
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