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Synthesis of novel oxa-isosteres of spermidine and spermine

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
35
Issue
21
Identifiers
DOI: 10.1016/s0040-4039(00)73252-7

Abstract

Abstract 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.

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