Enynes, easily obtained by the Sonogashira coupling reactions of aromatic iodides, undergo, with good yields, enyne metathesis using the Grubbs catalyst. The resulting dienes are interesting carbo- and heterocycles which can give complex natural frameworks by Diels–Alder reactions. Thus, an estradiol type skeleton is obtained in two steps from the corresponding enynes. An example of a metathesis-Diels–Alder cascade one-pot process is reported.