1-({4-(tert-Butyl-dimethyl-silanyloxy)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidine-2-carbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester → 18-(tert-Butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl ester

Participants

Reaction Steps

The diene (125) (1 g, 1.6 mmol) was dissolved in degassed DCE (1000 ml), Hoveyda-Grubbs 2nd generation (100 mg, 0.16 mmol) was added and the reaction mixture was refluxed under an atmosphere of argon overnight. The reaction mixture was evaporated on silica and purified by column chromatography on silica gel (30% EtOAc in Heptane→50% EtOAc in Heptane) to give the title compound (470 mg, 0.767 mmol, 48%). M+H=614.

Provenance & Evidence