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ハイパーサンプロンMの総合成

Adrian E Samkian¹, Scott C Virgil¹, Brian M Stoltz¹

¹The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Journal of the American Chemical Society

|July 3, 2024

まとめ

研究者らは,ホモアダマンタンのポリサイクリックポリプレニル化アシルフローログルシノール (PPAP) の最初の完全な合成を達成しました. この突破は,サイクロペンテンの無効化と関連化合物のリング拡張を含む新しい戦略を使用した.

科学分野:

有機化学
自然製品合成

背景:

ポリサイクルポリプレニルアシログルシノール (PPAP) は,多様な生物学的活動を持つ自然製品のクラスです.
ホモアダマンタン PPAPは,独特のケージのような構造で特徴づけられ,重要な合成課題を提示しています.

研究の目的:

代表的なホモアダマンタンPPAPであるハイパーサンポンの最初の完全合成を報告する.
関連するホモアダマンタン PPAPのための潜在的に一般的な合成戦略を開発する.

主な方法:

合成はサイクロヘクセノンから始まった.
主なステップは,サイクロペンテンの無効化と,ヒドラズレン中間物質の形成のためのリング拡張であった.
この戦略は,合成を完了するために予期せぬ遅い段階の変換を含んでいた.

主要な成果:

ハイパーサンポンの最初の完全合成が完了しました.
関連するホモアダマンタン PPAPに対応する新合成経路の実証
難易度の高いヒドラズレン形成およびその後の改変を含む主要な反応経路の解明.

結論:

報告された合成は,ハイパーサンポーンMおよびそのアナログへの貴重な経路を提供します.
開発された戦略は,ホモアダマンタン PPAPのエスカフォールドにアクセスするための一般的なアプローチを提供します.
この研究は複雑な天然製品の合成のための合成ツールボックスを拡張します.

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