Abstract Pathways to synthesize germacranolides with ether bridges between C 1 and C 5 or C 3 and C 10 were described. A joint precursor was prepared using a readily available and inexpensive compound as starting material. The key step in the preparation of dihydropyranone-germacranolides proved to be a one-pot procedure involving several transformations, induced by the iodotrimethylsilane/acetonitrile system.