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

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.

Citation

Paul Massé, Sabine Choppin, Lucia Chiummiento, Françoise Colobert, Gilles Hanquet. Access to 12-Membered Cyclic ortho,meta-Diarylheptanoids: Total Synthesis of Actinidione via Isomyricanone. The Journal of organic chemistry. 2021 Feb 05;86(3):3033-3040

Mesh Tags

Substances

PMID: 33475349

search → result