Coupling of two differently substituted 1, 3-diaminopropane units 5 and 6 (Schemes 1 and 2) lead to the key intermediate 8, a tetra-N-protected spermine derivative. By selective deprotection and alkylation with (E)-4-(mesy1oxy) cinnamoyl chloride, followed by deprotection, 8 was transformed to the target spermine derivative 19. By an alternative route, the 1, 3-diaminopropanes 10 and 11 were combined to the tri-N-protected tetraamine 12. ...