The total synthesis of 4-deoxy-D,L-daunosamine

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Abstract
The aminosugar 4-deoxy-D,L-daunosamine and its derivatives were synthesized starting with 2,4-pentanedione which was converted to the key intermediate oxazolino-α-pyrone (19) by enamine formation with morpholine, oxidation with benzoyl peroxide, condensation with ammonium acetate, bromination with N-bromosuccinimide, nitrile formation, acid hydrolysis, and cyclization with thionyl chloride. Hydrogenation of 19 gave the δ-lactone 22 which was converted to 4-deoxy-D,L-daunosamine derivatives by reducing the lactone ring to the corresponding hemiacetal 26.