A synthesis of bredinin (Mizoribine®) from an acyclic precursor |
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Authors: | Robert W HumbleDanielle F Middleton Joseph BanoubDavid F Ewing Andrew N Boa Grahame Mackenzie |
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Institution: | a Department of Chemistry, University of Hull, Cottingham Road, Kingston upon Hull HU6 7RX, UK b Department of Fisheries and Oceans, Northwest Atlantic Fisheries Centre, Science Branch, PO Box 5667, St. John’s, Newfoundland, Canada |
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Abstract: | Bredinin (4-carbamoyl-1-β-d-ribofuranosylimidazolium-5-olate, 1) was synthesised by the formation of a malonamate 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. |
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Keywords: | Nucleoside 5-Hydroxyimidazole Cyclisation |
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