title: Synthesis of a potent rhodomycin, oxaunomycin, and its analogs.
abstract: Oxaunomycin (3) and its regioisomer (6) were synthesized by employing regioselective glycosidations of the C-7 hydroxyl group of 10-O-acetyl-beta-rhodomycinone (16) and the C-10 hydroxyl group of the C-7,9-O-phenylboronate (14), respectively, in the presence of trimethylsilyl trifluoromethanesulfonate. Under the Königs-Knorr conditions, 16 was also glycosidated to provide a fluoro sugar analog (7).
authors.affiliation: Faculty of Pharmaceutical Sciences, Osaka University, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Kita
authors.forename: H
authors.initials: H
authors.lastname: Maeda
authors.forename: M
authors.initials: M
authors.lastname: Kirihara
authors.forename: Y
authors.initials: Y
authors.lastname: Fujii
authors.forename: T
authors.initials: T
authors.lastname: Nakajima
authors.forename: H
authors.initials: H
authors.lastname: Yamamoto
authors.forename: Y
authors.initials: Y
authors.lastname: Tamura
authors.forename: H
authors.initials: H
authors.lastname: Fujioka
mesh_terms: D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D007536:Isomerism
chemical_list: D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; C049973:oxaunomycin