STEREOSELECTIVE SYNTHESIS OF D,L-ERYTHROSE-DERIVATIVES D,L-1,4-DIDEOXY-4-AMINOERYTHROSE-DERIVATIVES BEARING A BETA-LACTAM AT C-4

Acylnitroso dienophiles react with azetidinodiazepines 1, with high st ereoselectivity from the alpha-side, to give cycloadducts 2 and 3. Cat alytic osmylation of these latter compounds proceeded with total face- selectivity to give diols 4 and 8, respectively. Hydrogenolysis, follo wed by molecular rearrangements, ultimately led to dideoxyaminoerythro se derivatives 6 (from 4) and to erythrose derivatives 10 (from 8). Th e hydrochlorides of 6a and 6b were assessed for their anti-HIV in vitr o activity; they were found to be less potent than castanospermine. (C ) 1996 Elsevier Science Ltd.