Synthesis of the tricyclic core of colchicine via a dienyne tandem ring-closing metathesis reaction

François-Didier Boyer (1) , Issam Hanna (2)

1 UCB - Chimie Biologique
2 DCSO - Laboratoire de synthèse organique

The synthesis of the tricyclic framework of colchicine has been achieved using a tandem ring-closing metathesis reaction of dienynes as the key step. In this process, both seven-membered rings B and C were formed in one step. Oxidation of tertiary allylic alcohol derived from the tandem metathesis product furnished an intermediate in the total synthesis of colchicine. © 2007 American Chemical Society.

Domaines: Chimie organique

François-Didier Boyer, Issam Hanna. Synthesis of the tricyclic core of colchicine via a dienyne tandem ring-closing metathesis reaction. Organic Letters, 2007, 9 (12), pp.2293-2295. ⟨10.1021/ol070708j⟩. ⟨hal-00951293⟩