The object of the proposed research will be to develop new methods for the synthesis of macrocyclic polyamine lactams. Among the members of this group of biologically active compounds are the spermine and spermidine alkaloids. Our methods will include the study of procedures for successive ring expansion of smaller heterocyclic systems to form the macrocyclic units. Transamidation of Beta-lactams has already been effective as a key step in the synthesis of homaline, celacinnine and dihydroperiphylline. This method along with other newly developed ring-expansion sequences will be utilized for the synthesis of ephedradine-A, chaenorin, pleurostylin, palustrine and cyclocelabenzene.