Stereoselective synthesis of (7Z,11Z)-octadeca-7,11-diene-1,18-dioic acid was carried out using reaction Ti-catalyzed homo-cyclomagnesiation of 2-(nona-7,8-dien-1-yloxy)tetrahydro-2H-pyran. By intermolecular esterification of dicarboxylic acid with polyether acetylene alcohols in the presence of DCC and DMAP, the corresponding diesters were synthesized in good yields (67-75%). Based on symmetric diesters with terminal triple bonds, polyether macrodiolides containing conjugated triple bonds and pharmacophoric 1Z,5Z-diene fragments in their structure were synthesized for the first time.