Synthesis of a potent rhodomycin, oxaunomycin, and its analogs.
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).
Kita
Y
Y
Faculty of Pharmaceutical Sciences, Osaka University, Japan.
Maeda
H
H
Kirihara
M
M
Fujii
Y
Y
Nakajima
T
T
Yamamoto
H
H
Tamura
Y
Y
Fujioka
H
H
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D007536:Isomerism
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; C049973:oxaunomycin