A short and efficient transformation of rhamnose into activated daunosamine, acosamine, ristosamine and epi-daunosamine derivatives, and synthesis of an anthracycline antibiotic acosaminyl-epsilon-iso-rhodomycinone.
3-Amino-2,3,6-trideoxyhexopyranoses are essential constituents of most anthracycline antitumour antibiotics. For an investigation of structure-activity relationships, the four diastereomeric amino sugars daunosamine, acosamine, ristosamine, and epi-daunosamine were synthesised in short and efficient routes starting from commercially available rhamnose. Several glycosyl donors were provided and their use was exemplified in the synthesis of acosaminyl-epsilon-isorhodomycinone.
Renneberg
B
B
Institute of Organic Chemistry, University of Göttingen, Germany.
Li
Y M
YM
Laatsch
H
H
Fiebig
H H
HH
D018943:Anthracyclines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004317:Doxorubicin / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006595:Hexosamines / Q000138:chemical synthesis* / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D012210:Rhamnose / Q000737:chemistry*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D006595:Hexosamines; C066033:7-O-(3-amino-2,3,6-trideoxy-alpha-hexopyranosyl)-epsilon-isorhodomycinone; C015490:rhodomycinone; C007217:daunosamine; C010783:ristosamine; C010669:acosamine; D004317:Doxorubicin; D012210:Rhamnose