Synthesis of novel oxa-isosteres of spermidine and spermine

Article abstract of DOI:10.1016/S0040-4039(00)73252-7

3-Bromopropylamine hydrobromide reacts with N-hydroxyphthalimide in the presence of DBU to give, not the expected N-(3-aminopropyloxy)phthalimide, but N-(3-aminooxypropyl)-phthalimide, 6, formed by an unusual intramolecular rearrangement. Coupling of the pentamethyl-chroman-6-sulphonyl (Pmc) derivatives of 9 and 13 with N-Bpoc-aminopropanol affords a differentially protected 6-oxaspermidine 10 and 6,9-dioxaspermine 14 respectively from which the protecting groups are removed independently.