Using simplified model derivatives, the assembly of the macrocyclic rings of madangamines, including the 13- and 14-membered D rings of madangamines C–E, the all-<i>cis</i>-triunsaturated 15-membered D ring of madangamine A, and the (<i>Z</i>,<i>Z</i>)-unsaturated 11-membered E ring common to madangamines A–E, has been studied