Synthetic routes to coriolin 1 were studied. The key bicyclic intermediate 3 corresponding to the A/B rings of 1 was synthesized from dicyclopentadiene through several steps. The highly functionalized B/C moiety model 44 was obtained from 22. Possible intermediates 52, 53, 54 and 55 for the biosynthesis of coriolin were synthesized through 50.