Lithium and proton templated ω-polyazamacrolactamization, new general routes to macrocyclic polyamines

A general, lithium templated/catalyzed ω-polyazamacrolactamization method for the synthesis of macrocyclic polyamines including spermidine and spermine alkaloids is presented. The formation of 12-, 13-, 16-, 17-, and 19-membered N3, N4, N5, and N6 containing rings is described. A proton templated/catalyzed macrolactamization of some ω-polyazaaminoesters is also observed.