Synthese von N 1 ,4‐Di( p ‐cumaroyl)spermin, einem möglichen Biogenese‐Vorläufer von Aphelandrin

Synthesis of N 1 ,4‐Di( p ‐coiimaroyl)spermine, a Possible Biogenetic Precursor of Aphelandrine 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‐(mesyloxy)cinnamoyl chloride, followed by deprotection, 8 was transformed to the target spermine derivative 19 . By an alternative route, the 1,3‐diaminopiopanes 10 and 11 were combined to the tri‐ N ‐protected tetraamine 12 . The intermediates 8 and 12 can be used for the preparation of polyamine derivatives.