A number of polyamine era-analogues 14a-d, 19 have been synthesised. S
permidine era-analogues and homologues 14 were made from N-(aminooxypr
opyl)phthalimide 8a which was obtained either from the Fmoc-deprotecti
on of N-[3-(Fmoc-amino)propoxy]phthalimide 4a or from the reaction bet
ween 3-bromopropylamine and N-hydroxyphthalimide, both reactions invol
ving an unusual rearrangement mechanism. Sulphonated derivatives 9, 16
, upon Mitsunobu condensation with N-protected 3-aminopropanol or N-al
kylation with N-(bromoalkyl)phthalimides, afforded the fully protected
spermidine and spermine oxa-analogues and homologues. Subsequent sequ
ential deprotection gave spermidine analogues 14. Using the same strat
egy, spermine oxa-analogue 19 was synthesised.