The compact synthesis of a new ring fused benzo [b] thieno derivative with an embedded nine-membered ring system via ring closing metathesis methodology is described. The preparation of the novel 11H-benzo [b] thieno [2, 3-c] pyrrolo [2, 3-a] indol-11-one via palladium-mediated oxidative cyclisation of benzo [b] thien-2-oyl indole derivatives is also reported.