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A synthesis of bredinin (Mizoribine®) from an acyclic precursor

Humble, Robert W.; Middleton, Danielle F.; Banoub, Joseph; Ewing, David F.; Boa, Andrew N.; Mackenzie, Grahame


Robert W. Humble

Danielle F. Middleton

Joseph Banoub

David F. Ewing


Bredinin (4-carbamoyl-1-β-D-ribofuranosylimidazolium-5-olate, 1) was synthesised by the formation of amalonamate from 2,3-isopropylidene-D-ribofuranosylamine and ethyl malonyl chloride, followed by a sequence involving amination, via reduction of an oxime, heterocycle formation and then deprotection.


Humble, R. W., Middleton, D. F., Banoub, J., Ewing, D. F., Boa, A. N., & Mackenzie, G. (2011). A synthesis of bredinin (Mizoribine®) from an acyclic precursor. Tetrahedron letters; the international organ for the rapid publication of preliminary communications in organic chemistry, 52(47), 6223-6227.

Journal Article Type Article
Acceptance Date Sep 16, 2011
Online Publication Date Sep 22, 2011
Publication Date Nov 23, 2011
Journal Tetrahedron Letters
Print ISSN 0040-4039
Electronic ISSN 1873-3581
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 52
Issue 47
Pages 6223-6227
Keywords Nucleoside; 5-Hydroxyimidazole; Cyclisation
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