Furfuryl derivatives 3 with an allyl ether or allylamine type linkage to a methylenecyclopropane moiety readily undergo intramolecular Diels-Alder reactions at 10-12 kbar to yield interesting new spirocyclopropane-annelated tricyclic structures 4 diastereoselectively in excellent yields. The starting materials 3 are readily obtained by Pd0-catalysed nucleophilic allylic substitution on 1-chloro-1-ethenylcyclopropane 1 with furfurol or furfurylamine. Some acid-catalysed ring-openings of the 7'-methoxy derivative 4d are described as well. Furthermore, activation parameters for the intramolecular cycloaddition of 3a have been determined by means of on-line infrared spectroscopy under high pressure.