Access to 12-Membered Cyclic ortho,meta-Diarylheptanoids: Total Synthesis of Actinidione via Isomyricanone,The Journal of Organic Chemistry

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Access to 12-Membered Cyclic ortho,meta-Diarylheptanoids: Total Synthesis of Actinidione via Isomyricanone
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-01-21 , DOI: 10.1021/acs.joc.0c02489
Paul Massé ₁ , Sabine Choppin ₁ , Lucia Chiummiento ₂ , Françoise Colobert ₁ , Gilles Hanquet ₁

Affiliation

We describe herein the first access to 12-membered cyclic[7,0]ortho,meta-diarylheptanoids. The key features of the synthesis include both a Suzuki–Miyaura coupling and a ring closing metathesis. Actinidione, a promising natural product, along with a bioactive tetracyclic derivative were obtained in 14 steps for the first time from cheap commercially available substrates with an overall yield of 18–21%. Our modus operandi complies with the principles of the synthesis ideality by using notably strategic reactions.

中文翻译：

进入12成员的环状邻位，间-二芳基庚烷类化合物：通过异麦芽酮酮合成放线菌酮

我们在此描述〜12元环[7,0]第一接入邻，间位-diarylheptanoids。合成的关键特征包括Suzuki-Miyaura偶联和闭环易位。放线菌酮，一种有前途的天然产物，以及具有生物活性的四环衍生物，是第14步首次从廉价的市售底物中获得，总收率为18-21％。我们的作案手法通过使用显着的战略反应来符合综合理想化的原则。

更新日期：2021-02-05

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