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

Paul Massé | Zendy; Sabine Choppin | Zendy; Lucia Chiummiento | Zendy; Françoise Colobert | Zendy; Gilles Hanquet | Zendy

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

Author(s) -

Paul Massé,

Sabine Choppin,

Lucia Chiummiento,

Françoise Colobert,

Gilles Hanquet

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.0c02489

Subject(s) - chemistry , diarylheptanoids , metathesis , yield (engineering) , total synthesis , derivative (finance) , ring closing metathesis , combinatorial chemistry , salt metathesis reaction , ring (chemistry) , natural product , stereochemistry , organic chemistry , materials science , economics , financial economics , metallurgy , polymerization , polymer

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.

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