Synthese von N1,4‐Di(p‐cumaroyl)spermin, einem möglichen Biogenese‐Vorläufer von Aphelandrin

Abstract

Synthesis of N1,4‐Di(p‐coiimaroyl)spermine, a Possible Biogenetic Precursor of AphelandrineCoupling 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.