This paper reports the synthesis of polyene oligomers ("oligoenes") that contain up to 15 double bonds that are identical to the "all five-membered ring" species formed through cyclopolymerization of diisopropyldipropargylmalonate. The oligoenes contain an isopropylidene unit at each end. The isolated oligoenes range from the "dimer" (a pentaene, (E)-di-1,2-[1-(2-methyl-propenyl)-4,4-di-iso-propyl-carboxy-cyclopent-1-enyl]-ethene (3b(2))) to the "heptamer" (3b(7), a pentadecaene). Oligoenes 3b(2), 3b(3), 3b(4), 3b(5), and 3b(7) were prepared through Wittig-like reactions between aldehydes and the appropriate monometallic Mo alkylidene or bimetallic Mo bisalkylidene species whose alkylidene is derived from an identical five-membered ring monomeric unit. Compounds 3b2, 3b4, and 3b(6) were prepared through McMurry coupling reactions of aldehydes. A representative aldehyde (the "monomeric" aldehyde) is diisopropyl-3-formyl-4(2-methylprop-1-enyl) cyclopent-3-ene-1,1-dicarboxylate (2b), McMurry coupling of which yields 3b(2). A heptaene that contains a six-membered ring in the central unit also was prepared in a Wittig-like reaction involving a bimetallic Mo alkylidene; this species is a model for oligoenes that contain both six-membered and five-membered rings. X-ray structures of two bimetallic species that are employed in the synthesis of the oligoenes are reported.