Suitable entry to a 10-membered ring with eleutheside functionality through Nozaki–Hiyama condensation

Access to a medium-sized unit of 15-seco-eleutheside analog 19 has been opened through the NiCl2/CrCl2-mediated intramolecular condensation of iodoaldehyde 8 with excellent yields. Transformation of the phenylcyclononanol 15 into the tetracyclic analog 19 was achieved in a four-step sequence with 65% overall yield.