Starting from various acetylenedicarboxylates (1a-e) as bis-dienophiles and [2.2](3,4)furanophane (2) as bis-diene, a series of ribbon-type oligomers (6) has been prepared via repetitive Diels-Alder reactions. Intramolecular Diels-Alder cycloaddition of 5, the smallest "AB-type" building block of 6, provides cage compound 7, whose structure has been determined unambiguously by crystallography. In order to avoid competitive retro-Diels-Alder reactions, high-pressure conditions have been applied. This approach provides ribbon-type polymers which contain cyclooctadiene (COD) moieties as "semiflexible" units.