Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
J Org Chem. 2012 Sep 21;77(18):7850-7. doi: 10.1021/jo301007x. Epub 2012 Sep 4.
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.
在有机催化剂 5 的存在下，对毛地黄毒苷 C 进行酰化反应，以高达 90%的区域选择性（催化剂控制的区域选择性）得到 C(4'''')-O-酰化物。通过混合酸酐法，在 5 或相关的有机催化剂存在下，可以在 C(4'''')-OH 上引入各种官能化的酰基。另一方面，DMAP 催化的毛地黄毒苷 C 酰化反应以高达 97%的区域选择性（底物控制的区域选择性）得到 C(3'''')-O-酰化物。因此，毛地黄毒苷 C 的八个游离羟基中的酰基可以实现多种区域选择性引入。
