Ruthenium-Catalyzed Cross Metathesis of [beta]-Myrcene and its Derivatives with Methyl Acrylate

The reaction of [beta]-myrcene with methyl acrylate produces 3-methylenecyclopent-1-ene in the presence of the Ru catalyst Neolyst M2 by ring-closing metathesis in the first step. In the second step, the generated methylidene unit reacts with methyl acrylate to give the corresponding unsaturated cyclic ester by cross metathesis. Under the optimized reaction conditions (80°C, Neolyst M2, 16equivalents of methyl acrylate), derivatives of [beta]-myrcene, myrcenol, myrcenyl acetate, and [beta]-ocimene, react to yield functionalized acyclic esters.