Regioselective Diversification of a Cardiac Glycoside, Lanatoside C, by Organocatalysis

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• 作者：Yoshihiro Ueda ; Kenji Mishiro ; Keisuke Yoshida ; Takumi Furuta ; Takeo Kawabata
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：September 21, 2012
• 年：2012
• 卷：77
• 期：18
• 页码：7850-7857
• 全文大小：449K
• 年卷期：v.77,no.18(September 21, 2012)
• ISSN：1520-6904

文摘

Acylation of lanatoside C in the presence of organocatalyst 5 gave the C(4鈥测€测€测€?-O-acylate in up to 90% regioselectivity (catalyst-controlled regioselectivity). Various functionalized acyl groups can be introduced at the C(4鈥测€测€测€?-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鈥测€测€测€?-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.