変換誘導レトロ合成戦略の計算拡張により,パスパリンAとエミンドールPBの総合成が可能
Daria E Kim1, Joshua E Zweig1, Timothy R Newhouse1
1Department of Chemistry , Yale University , 225 Prospect Street , New Haven , Connecticut 06520-8107 , United States.
Journal of the American Chemical Society
|January 11, 2019
まとめ
研究者は,パスパリンAとエミンドールPBの2つのインドルディテルペノイドの全合成を達成しました. この研究は合成化学と量子計算を組み合わせて 自然製品の合成を簡素化しました
科学分野:
- 有機化学
- 自然製品合成
- コンピュータ化学
背景:
- インドール・ディターペノイドは,重要な生物学的活動を持つ複雑な天然製品の一種である.
- これらの分子全体の合成は,複雑な構造のためにかなりの課題を提示します.
研究 の 目的:
- エミンドールPBの最初の完全合成を報告し,その構造を確認する.
- パスパリンAの簡潔な全合成を図る
- 効率的な合成経路設計のために,計算化学をレトロ合成分析に統合する.
主な方法:
- 商用材料から9段階のパスパリンAの合成
- エミンドールPBの合成は13段階で行われる.
- 密度関数理論 (DFT) の計算を使用して,主要なカルボカチオンの再配置を予測し,分析する.
- 計算化学を用いて 逆合成の断絶を誘導する
主要な成果:
- パスパリンAとエミンドールPBの合成が成功しました
- エミンドールPBのこれまで曖昧な構造の確認
- DFT計算は好ましい合成経路を正確に予測し,経験的スクリーニングを削減しました.
- 合成戦略の最適化における量子化学計算の有用性を示した.
結論:
- パスパリンAとエミンドールPBの全合成が成功しました.
- 計算化学は,エネルギー的に実現可能な断絶を特定することによって,レトロ合成設計を大幅に強化します.
- この統合されたアプローチは,天然製品の合成における合成の努力と資源の支出を最小限に抑えます.
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