The syntheses of two cyclodeca[ij]isoquinoline derivatives, which embody the carbon framework of stephaoxocanidine, excentricine and the recently isolated stephalonganines A, B and C, are reported. The target tricyclic compounds were prepared from isovanillin, employing a ring‐closing metathesis approach towards the synthesis of a benzocyclodecane‐type common intermediate; different modifications of thePomeranz–Fritsch protocol allowed the installation of the heterocyclic ring.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)