Weidong Wu, L. Ma, Li Zhang
Apr 1, 2000
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Influential Citations
8
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract 5-Phenyl-3-[(2′ R ,3′ S )-3′-hydroxy-2′-dimethoxymethyltetrahydrofuran-3′-yl]-1,2,4-oxadiazole 10a and its epimer 11a , 5-methyl-3-[(2′ R ,3′ S )-3′-hydroxy-2′-dimethoxymethyltetrahydrofuran-3′-yl]-1,2,4-oxadiazole 10b and its epimer 11b were synthesized from cyanohydrin benzoates 8a , 9a and cyanohydrin acetates 8b , 9b , respectively, by treatment with hydroxylamine in methanol via intramolecular transacylation and subsequent cyclization of the corresponding amidoximes. Hydrolysis and reduction of the dimethoxymethyl groups in the above compounds gave the desired compounds 12a , 13a , 12b and 13b.