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

Abstract : 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.