A short and efficient transformation of rhamnose into activated daunosamine, acosamine, ristosamine and epi-daunosamine derivatives, and synthesis ofan anthracycline antibiotic acosaminyl-epsilon-iso-rhodomycinone

3-Amino-2,3,6-trideoxyhexopyranoses are essential constituents of most anth racycline antitumour antibiotics. For an investigation of structure-activit y relationships, the four diastereomeric amino sugars daunosamine, acosamin e, ristosamine, and epi-daunosamine were synthesised in short and efficient routes starting from commercially available rhamnose. Several glycosyl don ors were provided and their use was exemplified in the synthesis of acosami nyl-epsilon -iso-rhodomycinone. (C) 2000 Elsevier Science Ltd. All rights r eserved.