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サイクロシトリノールの非対称的全合成

Junyang Liu¹, Jianlei Wu¹, Jian-Hong Fan¹

¹Department of Chemistry , Southern University of Science and Technology , Shenzhen 518055 , China.

Journal of the American Chemical Society

|April 5, 2018

まとめ

異常なC25ステロイドであるサイクロシトリノールの最初の非対称的全合成は18ステップで達成されました. 鍵となるII型内分子 [5 + 2] サイクロアディションにより,挑戦的なビサイクロ[4.4.1] A/Bリングシステムが効率的に構築された.

科学分野:

有機化学
合成化学
自然製品合成

背景:

サイクロシトリノールは複雑な構造を持つ珍しいC25ステロイドです.
複雑な天然製品の合成は有機化学において重要な課題を提示する.
非対称な合成は,エナチオメリックに純粋な化合物を得るために不可欠です.

研究の目的:

サイクロシトリノールの最初の非対称的合成を達成するために
独特のbicyclo[4.4.1] A/Bリングシステムを構築するための効率的な合成経路を開発する.
複雑なステロイド構造のための新合成方法論を探求する.

主な方法:

18段階の線形合成シーケンスが採用された.
商業的に利用可能な化合物11が,出発材料として使用された.
コアリングシステムを構築するために,II型内分子 [5 + 2] サイクロアディションが使用されました.

主要な成果:

サイクロシトリノールの最初の非対称的全合成が成功しました.
抗ブレットダブルボンドを備えた挑戦的なbicyclo[4.4.1] A/Bリングシステムは効率的に構築された.
サイクロアディション反応は高いダイアステレオ選択性で進行した.

結論:

開発された合成戦略は,サイクロシトリノールへの効果的な経路を提供します.
この研究は,複雑な多循環系を構成するII型内分子 [5 + 2] サイクル添加の有用性を示しています.
この合成は,サイクロシトリノールとその類似体の生物学的活動に関するさらなる調査の道を開きます.

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