Abstract
A new approach to the (±)-2-amino-2-deoxytetritol derivatives (1), (2) and (3) is described, starting either from the allylic trichloroacetimidate (5) or from the allylic trichloroacetamide (11). The 4,5-dihydro-oxazole (6), obtained by iodocyclization of the acetimidate (5), was hydrolysed to the corresponding amide (7) which, by treatment with CO32– on a polymeric support, afforded the cis-4,5-dihydro-oxazole (8). Cleavage of compound (8) and acetylation gave the erythro-derivative (1). On the other hand, iodocyclization of the amide (11) led to the trans-4,5-dihydro-oxazole (12a) which, after hydrolysis and basic treatment, was converted into the cis-4,5-dihydro-oxazole (14). After hydrolysis and acetylation, the erythro-derivative (2) was obtained in good yield. Alternatively, after hydrolytic cleavage of the trans-4,5-dihydro-oxazole (12a), treatment with AcO– on a polymeric support and acetylation gave the threo-derivative (3) in good yield.
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