Total Synthesis of (±)-Oxacyclododecindione,The Journal of Organic Chemistry

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Total Synthesis of (±)-Oxacyclododecindione
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-04-10 , DOI: 10.1021/acs.joc.4c00333
Kevin Seipp ₁ , Vincent Grölz ₁ , Hagen Glass ₁ , Elisabeth Quraishi ₁ , Nina Vierengel ₁ , Till Opatz ₁

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Racemic total synthesis of the natural product oxacyclododecindione, isolated in 2008 as the first member of the oxacyclododecindione family, is reported. Studies toward this molecule commenced with a biomimetic late-stage C–H oxidation starting from 14-deoxyoxacyclododecindione as a known precursor. This provided insights into the reactivity of the macrolactone class but did not permit the synthesis of the target natural product. Based on these results, a synthetic strategy through intramolecular Friedel–Crafts acylation combined with Barton decarboxylation to introduce the tertiary alcohol, a major challenge in previous synthetic efforts, was envisioned. This resulted in an 11-step racemic total synthesis of (±)-oxacyclododecindione, renowned for its potent anti-inflammatory and antifibrotic activities.

中文翻译：

（±）-氧杂环十二烷二酮的全合成

据报道，天然产物 oxacyclododecindione 的外消旋全合成于 2008 年分离，是 oxacyclododecindione 家族的第一个成员。对该分子的研究始于 14-脱氧环十二烷二酮作为已知前体的仿生晚期 C-H 氧化。这提供了对大内酯类反应性的见解，但不允许合成目标天然产物。基于这些结果，设想了一种通过分子内 Friedel-Crafts 酰化结合 Barton 脱羧引入叔醇的合成策略，这是以前合成工作中的一个主要挑战。这导致了（±）-氧氧环十二烷二酮的 11 步外消旋全合成，该合成以其强大的抗炎和抗纤维化活性而闻名。

更新日期：2024-04-10

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