jo6b01265_si_004.cif (1.64 MB)
Synthesis of Ocotillol-Type Ginsenosides
dataset
posted on 2016-07-11, 00:00 authored by Renzeng Shen, Xin Cao, Stephane Laval, Jiansong Sun, Biao YuA total
of 14 ocotillol-type ginsenosides were conveniently synthesized employing
glycosylation of ocotillol sapogenin derivatives with glucosyl ortho-alkynylbenzoate donors under the promotion of a gold(I)
catalyst as the key step. Relying on a rational protecting group strategy
and the unexpected regioselectivity of the glycosylation of the 3,25-diol
sapogenins (2a/2b, 5a/5b) for the tertiary 25-OH, mono 3-O-glucosyl
ocotillol-PPD, 6-O-glucosyl ocotillol-PPT, 25-O-glucosyl ocotillol-PPD/PPT and 3,25-di-O-glucosyl ocotillol-PPD/PPT ginsenosides were prepared in which the
configuration at the C-24 is either R or S.
