非従来の断片の使用は, (-) - カリスポンジオリドの簡潔な総合成を可能にします
Francesco Manoni1, Corentin Rumo1, Liubo Li1
1Department of Chemistry and Biochemistry, University of California-Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States.
Journal of the American Chemical Society
|January 16, 2018
まとめ
この研究では (-) - カリスポンジオリドの新しい非対称合成を詳細に説明し,マクロリドコアをディサカリドとモノテルペンから構築した. この革新的なアプローチは,断片結合のためのキラルイリジウム触媒と,マクロラクトニゼーションのためのユニークな断片化戦略を使用しています.
科学分野:
- 有機化学
- 合成化学
- 自然製品合成
背景:
- (-) カリスポンジオリドは生物学的活性を持つ複雑な海洋産物です.
- マクロリドへの以前の合成経路は,しばしば挑戦的なセコ酸中間物質を含む.
研究 の 目的:
- 新しく効率的な (-) - カリスポンジオリドの合成を開発する.
- セコ酸中介物質を避け,マクロライドコアの構築のための非典型的戦略を探求する.
主な方法:
- 断片結合のためのキラルイリジウム触媒を用いた非対称合成.
- 主要な中間物質のステレオ選択的および地域選択的構成は,周周周分解による.
- マクロサイクル形成のための炭酸性マクロラクトニゼーション.
主要な成果:
- (-) - カリスポンジオリドの直接的かつ柔軟な合成が達成されました.
- マクロリドドメインは非典型的にディサカリドとモノテルペンから構成される.
- 合成の過程でステレオケミカルとレジオケミカル制御が維持された.
結論:
- 記述された合成経路は,マクロライド合成のための新しいパラダイムを提供します.
- この方法は, (-) - カリスポンジオリドや他の複雑なマクロリドへの柔軟かつ効率的なアクセスを提供します.
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