Diels-Alder reactions of naphthoquinones with substituted hydroxybutadienes
containing a carbohydrate moiety proceed in a regioselective fashion, yiel
ding the corresponding C-glycosylated anthraquinones. A nucleoside having a
n anthraquinone fragment was synthesized by removal of isopropylidene prote
ction from C-glycosylated anthraquinone, followed by reaction with silylate
d 5-methyluracil. An O-formyl erythrose derivative containing an anthraquin
one fragment was obtained by acid hydrolysis of C-glycosylated anthraquinon
e and subsequent periodate cleavage of the hydrolysis product.