Synthesis of the tricyclic core of colchicine via a dienyne tandem ring-closing metathesis reaction.
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.
Boyer
François-Didier
FD
Unité de Chimie Biologique, AgroParisTech, INRA, F-78026 Versailles, France.
Hanna
Issam
I
D000480:Alkynes / Q000737:chemistry*; D003078:Colchicine / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism
D000480:Alkynes; D003078:Colchicine