THE SYNTHESIS OF OXA-ANALOGS AND HOMOLOGS OF NATURALLY-OCCURRING POLYAMINES

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.