Synthesis of Acarnidines: Guanidinated Spermidine Homologs Through Imine Intermediates

Abstract

One of the naturally occurring acarnidines , N-(5-guanidinopentyl)-N-[3-(3-methylbut-2-enamido) propyl ] dodecanamide, together with 17 analogues containing different alkyl chain lengths in the triamine structure and the acyl side chain, have been synthesized by a versatile general method whose key features are formation of the secondary amine by reductive amination of an aldehyde and incorporation of the guanidine function in the last step. This general method affords high yields of selectively substituted unsymmetric triamines.