The synthesis of a range of new compartmental macrocyclic complexes based on 2,6-diformyl and -diketo phenol groups is described. The metal-free ligands have been prepared and structurally characterised for the first time, and this has led to the synthesis of novel cubane and platinum-group metal complexes. The synthesis of related dithiophenolato-bridged compartmental complexes of Ni-II Cu-II and Zn-II has been achieved and the relevance of these species to metalloproteins is discussed.