エナンチオセレクティブ・トータル・シンセシス (+) - アルボリジニン
Zhen Zhang1, Sujun Xie1, Bin Cheng1
1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering , Lanzhou University , Lanzhou 730000 , China.
Journal of the American Chemical Society
|April 9, 2019
まとめ
研究者は,ケージ状のアルカロイド (+) - アルボリジニンの最初のエナンチオセレクティブ・トータル合成を報告した. この効率的な14段階の合成は,鍵となるステレオ選択反応を用いて,複合的なバイサイクルコアと四次ステレオセンターを構成する.
科学分野:
- 有機化学
- 合成化学
- 自然製品合成
背景:
- 状のアルカロイドは,生物学的に重要な複雑な構造を持っています.
- (+) - アルボリジニンのようなアルカロイドの総合成は,有機化学において相当な課題である.
研究 の 目的:
- 自然産物 (+) -アルボリジニンの効率的でエナント選択的な全合成を開発する.
- 複雑なアルカロイド構造を拡大する 強力な合成経路を確立する
主な方法:
- アザ[3.3.1]バイサイクルコアを構成するステレオセレクティブのダブルマニッヒ反応.
- C10ステレオセンターをセットする.
- C3四次中心とケージシステムを形成する内分子脱オロマティブアルキル化.
- C11ヒドロキシル基を設置するために,コバルト触媒による後期デカルボキシル化アセトキシル化.
主要な成果:
- (+) - アルボリジニンの14段階の非対称的全合成が達成されました.
- 合成により,アザ[3.3.1]双回転核と2つの四次ステレオセンターが急速に構築された.
- マイケル添加とオロマティブアルキル化を含む重要な変換が成功しました.
- ほとんどの反応はデカグラムスケールで実施され,スケーラビリティが実証されました.
結論:
- 報告された合成は (+) - アルボリジニンの有効な経路を提供する.
- この戦略は,複雑な分子合成におけるステレオ選択反応の力を強調しています.
- 合成のスケーラビリティは,アーボリジニンとその類似物のさらなる調査のための道を開きます.
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