TOTAL ASYMMETRIC-SYNTHESIS OF 3-AMINO-3-DEOXY-L-TALOSE AND DERIVATIVES

,4R)-2-exo-Cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1S')-camphanate [( +)-1, Diels-Alder adduct of furan to 1-cyanovinyl (1S)-camphanate] was transformed with high stereoselectivity into 10-dioxa-5-azatricyclo[5 .2.1.0(2,6)]dec-4-en-9-one [(+)-10]. Bromination of the corresponding (tert-butyl)dimethylsilyl enol ether [(-)-11], followed by Baeyer-Vill iger oxidation and then alkaline methanolysis provided methyl o-2-O,3- N-benzoyl-3-deoxy-alpha-L-talofuranuronate [(-)-17], the reduction of which gave hydro-2-O,3-N-benzoyl-3-deoxy-alpha-L-talofuranose [(-)-19] . Treatment with aqueous HCl furnished 3-amino-3-deoxy-L-talose hydroc hloride [(-)-2].