Application of the Grubbs ring-closing metathesis for the construction of a macrocyclic ansa-bridge. Synthesis of the tricyclic core of roseophilin

Article abstract of DOI:10.1016/S0040-4039(97)00424-3

Metalation/alkylation of the pyrrole-fused 10π anion 15 regiospecifically yields the β-alkylated ketones 16,17. Conversion of 17 to diene 24 followed by Grubbs ring-closing metathesis provides 29 which is transformed to the roseophilin tricyclic core structure 5.