Abstract
d-Ribono-1,4-lactone was treated with ethylamine in DMF to afford N-ethyl- d-ribonamide 9a in quantitative yield. Bromination of amide 9a by the system SOBr 2 in DMF or PPh 3/CBr 4 in pyridine led, after acetylation, to epoxide 7. However, treatment of amide 9a with acetyl bromide in dioxane followed by acetylation gave 2,3,4-tri- O-acetyl-5-bromo-5-deoxyl -N-ethyl- d-ribonamide 10a. Methanolysis of 10a, with sodium methoxide, afforded the N-ethyl- d-ribonolactam 11a in 51% overall yields. Using this method, N-butyl, N-hexyl, N-dodecyl, and N-benzyl- d-ribonolactams 11b– e were obtained in good yields (48–53%).
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