This invention relates generally to synthetic procedures that include the step of ring-opening metathesis of cyclic olefins and reaction with an acyclic diene co-reactant to produce olefin macrocycles by ring expansion, or alternatively. The ring expansion of the cyclic olefin is provided by three types of sequential olefin metathesis (ring-opening, cross, and ring-closing olefin metathesis). More particularly, the invention pertains to synthesis of olefin macrocycles via olefin metathesis reactions using a Group 8 transition metal complex as the metathesis catalyst. Macrocycles provided herein have a variety of uses in the pharmaceutical, biomedical, organic synthesis and chemical industries, such as the production of crown ethers that are useful as metal complexing species.