Synthesis of 5-substituted-3-[(2 ' S,3 ' S)-3 '-hydroxy-2 '-hydroxymethyltetrahydrofuran-3'-yl]-1,2,4-oxadiazoles and their epimers

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 epim er 11b were synthesized from cyanohydrin benzoates 8a, 9a and cyanohydrin a cetates 8b, 9b, respectively, by treatment with hydroxylamine in methanol v ia intramolecular transacylation and subsequent cyclization of the correspo nding amidoximes. Hydrolysis and reduction of the dimethoxymethyl groups in the above compounds gave the desired compounds 12a, 13a, 12b and 13b, (C) 2000 Elsevier Science Ltd. All rights reserved.