複合分子合成における触媒Z選択的交叉メタテシス:ディゾラゾールC1への収束型ステレオ選択的経路
Alexander W H Speed1, Tyler J Mann, Robert V O'Brien
1Department of Chemistry, Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467, United States.
Journal of the American Chemical Society
|November 8, 2014
まとめ
研究者らは,抗癌および抗真菌化合物であるディソラゾールC1の新合成を報告した. この方法は,複雑なマクロサイクル構造を効率的に構築するために,触媒Z選択的交叉メタテシスを利用します.
科学分野:
- 有機化学 オーガニック・ケミストリー
- 薬用化学 薬用化学について
- 自然製品合成 自然製品の合成
背景:
- ディゾラゾールC1は,重要な抗癌および抗真菌作用を有するマクロサイクルの天然製品です.
- 複雑な天然製品の効率的かつステレオ選択的合成は,薬剤の発見と開発に不可欠です.
研究 の 目的:
- ディゾラゾールC1.1.のコンバージェント,ダイアステレオセレクティブ,およびエナチオセレクティブの全合成を開発する.
- 複雑なマクロサイクルの構築における触媒Z選択クロスメタテシス (CM) の有用性を示します.
主な方法:
- Z-アルケニルボロナートエステル (B(pin)) とZ-アルケニルイオダイドのステレオ選択的合成のための触媒Z選択クロスメタテシス (CM) の適用.
- 単一段階の触媒的分子間および分子内クロスカップリング反応で,30基のマクロサイクルが形成されます.
主要な成果:
- 高いステレオ選択性を持つ複雑なZ-アルケニル-B ((pin)) とZ-アルケニルヨウ酸化物中間物の信頼性と効率的な合成.
- 臨界 (Z,Z,E) -トリエンの部分を含むディゾラゾールC1の30基のマクロサイクルを成功裏に構築した.
結論:
- 報告された合成経路は,ディソラゾールC1. 1にアクセスするための堅牢で効率的な方法を提供します.
- 触媒Z選択型CMは,複雑なポリエネを含むマクロサイクルのステレオ制御合成のための強力なツールです.
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