汎用シントンとしてのフラン:カリベノールAとカリベノールBの総合成
1Department of Chemistry and Center for Integrated Protein Science, Ludwig-Maximilians-Universität München , Butenandtstrasse 5-13, 81377 München, Germany.
Journal of the American Chemical Society
|February 21, 2017
まとめ
研究者は複雑なノードテルペノイドカリベノールAとBを合成し,複雑な分子構造を構築するための新しい方法を示し,フーランシントンの有用性を確認しました.
科学分野:
- 有機化学
- 自然製品合成
- 合成方法論の開発
背景:
- ノルディテルペノイドは,潜在的な生物学的活動を持つ複雑な天然製品です.
- これらの分子への効率的な合成経路は,さらなる調査に不可欠です.
- 以前の合成は,様々な構造的なモチーフへのアクセスに制限があります.
研究 の 目的:
- 複雑なノルドテルペノイドカリベノールAとBの新合成戦略を開発する.
- 関連する天然製品へのアクセスに関する 共通の構成要素のアプローチを確立する.
- 複合分子合成におけるフーラン誘導体の汎用性を実証する.
主な方法:
- 災害選択のフリデル・クラフトス・トリフレーションは7つの構成のリングを形成する.
- カリベノールA合成のためのフラン環の後期酸化.
- カリベノールB合成のための内分子有機触媒 α-アリレーション.
- 内分子アルドール添加と選択的な核愛性添加は,主要な構造特性に起因する.
主要な成果:
- 共通の前体からカリベノールAとBの合成に成功した.
- 7つの環のシステムへの効率的なルート開発
- サイクロペンテノン分子の構築のための新しい方法の確立.
- 複合合成におけるヌクレオフィルとシントンとしてのフランの有用性を示した.
- 第2世代のアンフィレクトライドを合成した
結論:
- 開発された合成戦略は,複雑なノルドテルペノイドへのアクセスを提供します.
- フランは有機合成において価値があり,多用途のシンソンが確認されている.
- 方法論は,関連する天然製品と類似品の合成を可能にします.
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