We report herein a concise route for the total synthesis of rapicone. The key strategy to form the ynone intermediate involves an Fe(III)/TEMPO-catalyzed aerobic oxidation of a 1,3-dihydroisobenzofuran moiety. This ether oxidation for the simultaneous installation of the keto aldehyde allowed the effective formation of the required ynone intermediate. The concise total synthesis of rapicone is substantiated by the unique formal [4 + 2] cycloaddition of acyl ketene with alkynone and is completed in 7 steps with 9.4% overall yield.

中文翻译：

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基于酰基乙烯酮-炔烃环加成反应的雷吡酮的合成


我们在此报告了雷吡酮全合成的简明路线。形成烯酮中间体的关键策略涉及 Fe（III）/TEMPO 催化的 1,3-二氢异苯并呋喃部分的有氧氧化。这种用于同时安装酮醛的醚氧化允许有效形成所需的 ynone 中间体。雷吡酮的简洁全合成通过酰基乙烯酮与炔烃酮独特的形式 [4 + 2] 环加成反应得到证实，分 7 步完成，总产率为 9.4%。