ハイドロキシcyclopropanolsの触媒カルボニラティブスピロラクトニゼーション
Dexter C Davis1, Katherine L Walker2, Chunhua Hu3
1Department of Chemistry and Center for Cancer Research, Purdue University , West Lafayette, Indiana 47907, United States.
Journal of the American Chemical Society
|July 27, 2016
まとめ
パラジアム触媒による新しい方法により,天然製品に含まれる 有価な化合物であるオクサスピロラクトンが効率的に合成されます. このスケーラブルな反応は 薬の発見と合成に役立つ 穏やかな条件と幅広い範囲を提供します
科学分野:
- 有機化学
- カタリシス
- 自然製品合成
背景:
- オクサスピロラクトンは,多くの複雑な天然製品で,重要な治療的可能性を持つ一般的な構造モチーフです.
- これらの有価な化合物への 効率的な合成経路は 薬の発見と開発に不可欠です
- 既存の方法は,複雑な分子合成に必要な効率性,範囲,または軽度が欠けている可能性があります.
研究 の 目的:
- パラジウム触媒による新型カスケードカルボニラティブ・スピロラクトニゼーション反応の開発
- オクサスピロラクトンを合成するための効率的でスケーラブルな方法を確立する.
- 複雑な天然製品の総合合成におけるこの方法の有用性を実証する.
主な方法:
- パラジウム触媒によるカスケードカルボニラティブ・スピロラクトニゼーション
- 水酸化プロパノール基質の準備のためのKulinkovich反応.
- 開発された方法論を用いた天然製品の総合合成.
- 高解像度電気スプレーイオン化質量スペクトロメトリ (ESI-MS) を使用したメカニズム研究.
主要な成果:
- 開発された方法は,軽度の反応条件下でオクサスピロラクトンを効率的に合成します.
- 高原子経済,広範囲の基板,およびスケーラビリティが実証されました.
- トルコの天然タバコ製品であるα-レヴァンタノリドとα-レヴァンタノリドの整体合成は,それぞれ2段階と4段階で行われました.
- メカニズム研究により,主要な中間物質と,触媒分解経路が特定されました.
結論:
- 新しく効率的なパラジウム触媒によるカスケード炭酸化スピロラクトニゼーションが確立された.
- この方法は,オクサスピロラクトンおよび関連する天然製品へのスケーラブルで汎用的な経路を提供します.
- この発見は複雑な治療薬の合成戦略の発展に寄与する.
関連する概念動画
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Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
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