Metathesis-based synthesis of 3-methoxy α,β-unsaturated lactones: total synthesis of (R)-kavain and of the C1-C6 fragment of jerangolid D

The total synthesis of (R)-kavain and of the C1-C6 fragment of jerangolid D has been achieved in nine and seven steps, respectively, from commercially available dimethyl d-malate. A metathesis reaction of vinyl ethers and a sulfoxide-modified Julia olefination have been employed as the key steps.