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

Abstract

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.

Citation

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. https://doi.org/10.1016/j.tetlet.2011.09.085

• 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
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 52
• Issue: 47
• Pages: 6223-6227
• DOI: https://doi.org/10.1016/j.tetlet.2011.09.085
• Keywords: Nucleoside; 5-Hydroxyimidazole; Cyclisation
• Public URL: https://hull-repository.worktribe.com/output/405528
• Publisher URL: https://www.sciencedirect.com/science/article/pii/S0040403911016182?via%3Dihub