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Article Dans Une Revue Journal of Organic Chemistry Année : 2021

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

Paul Massé
  • Fonction : Auteur
Sabine Choppin
Lucia Chiummiento
  • Fonction : Auteur
Françoise Colobert

Résumé

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.

Domaines

Chimie
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Dates et versions

hal-03228806 , version 1 (18-05-2021)

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Paul Massé, Sabine Choppin, Lucia Chiummiento, Françoise Colobert, Gilles Hanquet. Access to 12-Membered Cyclic ortho , meta -Diarylheptanoids: Total Synthesis of Actinidione via Isomyricanone. Journal of Organic Chemistry, 2021, 86 (3), pp.3033-3040. ⟨10.1021/acs.joc.0c02489⟩. ⟨hal-03228806⟩
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