Efficient synthesis of isofagomine and noeuromycin.
Starting from D-arabinose the synthesis of the very strong glycosidase inhibitors isofagomine (2) and noeuromycin (3) was achieved in six and seven steps, respectively. Keystep in the reaction sequence is the application of an efficient C-4 oxidation method to benzyl alpha-D-arabino-pyranoside. Subsequent Henry reaction of the obtained aldoketose with nitromethane provided the required branched carbohydrate precursors, which gave access to 2 and 3 in 17-21% overall yield.
Andersch
J
J
Department of Chemistry, University of Aarhus, Denmark.
Bols
M
M
D001089:Arabinose / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D050112:Imino Pyranoses; D010084:Oxidation-Reduction; D010880:Piperidines / Q000138:chemical synthesis*
D004791:Enzyme Inhibitors; D050112:Imino Pyranoses; D010880:Piperidines; C098432:isofagomine; C433123:noeuromycin; D001089:Arabinose; D006026:Glycoside Hydrolases; D005944:Glucosamine