Abstract: A number of polyamine oxa-analogues 14a–d, 19 have been synthesised. Spermidine oxa-analogues and homologues 14 were made from N-(aminooxypropyl) phthalimide 8a which was obtained either from the Fmoc-deprotection of N-[3-(Fmocamino) propoxy] phthalimide 4a or from the reaction between 3-bromopropylamine and N- hydroxyphthalimide, both reactions involving an unusual rearrangement mechanism. ...