Discriminatory silylation of hydroxymethyl and hydroxyethyl groups in the product of the Grieco lactone conversion. Approaches to the total synthesis of (±)-methylenolactocin

The racemic commercially available Grieco lactone was used as a starting material to synthesize new monocyclic precursors for the total synthesis of (±)-methylenolactocin. The key synthesis steps are the ozonolysis of the Grieco lactone derivative, preparation of regioisomeric silyl ethers, and Cu-catalyzed cross-coupling.