title: Regioselective diversification of a cardiac glycoside, lanatoside C, by organocatalysis.
abstract: Acylation of lanatoside C in the presence of organocatalyst 5 gave the C(4'''')-O-acylate in up to 90% regioselectivity (catalyst-controlled regioselectivity). Various functionalized acyl groups can be introduced at the C(4'''')-OH by a mixed anhydride method in the presence of 5 or the related organocatalyst. On the other hand, DMAP-catalyzed acylation of lanatoside C gave the C(3'''')-O-acylate in up to 97% regioselectivity (substrate-controlled regioselectivity). Thus, diverse regioselective introduction of acyl groups among eight free hydroxy groups of lanatoside C was achieved.
authors.affiliation: Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Ueda
authors.forename: Kenji
authors.initials: K
authors.lastname: Mishiro
authors.forename: Keisuke
authors.initials: K
authors.lastname: Yoshida
authors.forename: Takumi
authors.initials: T
authors.lastname: Furuta
authors.forename: Takeo
authors.initials: T
authors.lastname: Kawabata
mesh_terms: D000215:Acylation; D002301:Cardiac Glycosides / Q000737:chemistry*; D002384:Catalysis; D007799:Lanatosides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002301:Cardiac Glycosides; D007799:Lanatosides; C018548:lanatoside C