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Synthese von N 1 ,4‐Di( p ‐cumaroyl)spermin, einem möglichen Biogenese‐Vorläufer von Aphelandrin
Author(s) -
Veznik Frantisek,
Guggisberg Armin,
Hesse Manfred
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740322
Subject(s) - chemistry , spermine , derivative (finance) , polyamine , alkylation , stereochemistry , spermidine , chloride , medicinal chemistry , organic chemistry , biochemistry , financial economics , economics , enzyme , catalysis
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.