SYNTHESIS OF NOVEL OXA-ISOSTERES OF SPERMIDINE AND SPERMINE

Authors
LIN PKT MAGUIRE NM BROWN DM
Citation
Pkt. Lin et al., SYNTHESIS OF NOVEL OXA-ISOSTERES OF SPERMIDINE AND SPERMINE, Tetrahedron letters, 35(21), 1994, pp. 3605-3608
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
21
Year of publication
1994
Pages
3605 - 3608
Database
ISI
SICI code
0040-4039(1994)35:21<3605:SONOOS>2.0.ZU;2-8
Abstract
3-Bromopropylamine hydrobromide reacts with N-hydroxyphthalimide in th e presence of DBU to give, not the expected N-(3-aminopropyloxy)phthal imide, but N-(3-aminooxypropyl) phthalimide, 6, formed by an unusual i ntramolecular rearrangement Coupling-of the pentamethylchroman-6-sulph onyl (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 independentl y.