Herein, we disclose our results regarding various strategies toward the assembly of the octanylring of vinigrol. Attempts to generate the problematic eight-membered ring through a ring expansionor via unification of the terminal olefins using the ring-closing metathesis were not successful.The cyclooctane ring was created via a sequential hydroxy Diels−Alder/Claisen rearrangementreaction of diene 55 and N-benzylmaleimide.