Synthetic Investigation toward the D‐Ring‐Functionalized Cytotoxic Oleanane‐Type Saponins Pithedulosides D and E

  title={Synthetic Investigation toward the D‐Ring‐Functionalized Cytotoxic Oleanane‐Type Saponins Pithedulosides D and E},
  author={Shipin Ge and Yuan-Hong Tu and Jian‐Hui Xia and Jian-Song Sun},
  journal={European Journal of Organic Chemistry},
Leveraging on the orchestrated application of both Schmidt and Yu glycosylations, the first total syntheses of echinocystic acid saponins, pitheduloside D and E, the two antitumoral and representative D-ring functionalized oleanane-type saponins, were achieved. Benefited from the applied convergent synthetic strategy, the synthetic efficiency regarding the precious echinocystic acid could reach as high as 71% and 76% overall yields through 4 linear steps. 
3 Citations
Gold-catalyzed glycosylation in the synthesis of complex carbohydrate-containing natural products.
  • W. Li, Biao Yu
  • Chemistry, Medicine
  • Chemical Society reviews
  • 2018
The methodological developments in gold(i)- and gold(iii)-catalyzed glycosylation reactions are fully surveyed, which exploit the special alkynophilicity or the Lewis acidity of the gold cationicExpand
Site-selective C-H hydroxylation of pentacyclic triterpenoids directed by transient chiral pyridine-imino groups
It is found that Schönecker and Baran’s Cu-mediated aerobic oxidation can be applied and become site-selective on PT skeletons, as being effected unexpectedly by the chirality of the transient pyridine-imino directing groups. Expand
Synthesis of disaccharide modified berberine derivatives and their anti-diabetic investigation in zebrafish using a fluorescence-based technology.
The modification of berberine with carbohydrate groups could give derivatives with improved anti-diabetic activity, in particular the diglucose modified berberines derivative 1 which could dramatically promote the uptake of 2-NBDG in both zebrafish larvae and their eyes even at very low concentrations. Expand


Synthetic access toward the diverse ginsenosides
All the possible types of the protopanaxatriol and protopanaxadiol glycosides, the major active yet extremely heterogeneous principles of ginsengs, could be accessed by the present sequence ofExpand
A Highly Efficient Approach To Construct (epi)-Podophyllotoxin-4-O-glycosidic Linkages as well as Its Application in Concise Syntheses of Etoposide and Teniposide.
A highly efficient approach to construct the challenging (epi)-podophyllotoxin 4-O-glycosidic linkages was devised under the activation of a catalytic amount of a Au(I) complex, providing the desired glycosides in excellent yields. Expand
Synthetic Access Toward Cycloastragenol Glycosides.
Through the synthetic investigation, the reactivity sequence of the four OHs in cycloastragenol was fixed for the first time and a detour strategy for the highly efficient removal of bulky pivaloyl protecting groups was discovered. Expand
Concise synthesis of two trisaccharides related to the saponin isolated from Centratherum anthelminticum
Abstract Chemical synthesis of two trisaccharides related to the saponin isolated from Centratherum anthelminticum is reported. Stereoselective, high-yielding glycosylation strategies were developedExpand
Isolation and structures of avicins D and G: in vitro tumor-inhibitory saponins derived from Acacia victoriae.
Two new saponins named avicins D and G were isolated from the seed pods of the desert legume plant Acacia victoriae and exhibited potent cytotoxicity (apoptosis) against human T-cell leukemia (Jurkat cells) in vitro. Expand
Current synthesis of triterpene saponins.
The stereocontrolled glycosylation, global protection/deprotection, and the total synthesis of four unusual triterpene saponins are highlighted. Expand
Highly efficient synthesis of flavonol 5-O-glycosides with glycosyl ortho-alkynylbenzoates as donors.
With glycosyl ortho-alkynylbenzoates as donors, the highly efficient glycosylation of flavonoid 5-OH which are notorious for their low reactivity due to their involvement in the formation of strongExpand
Cytotoxic triterpenoid saponins of Albizia gummifera from the Madagascar rain forest.
Three new cytotoxic oleanane-type triterpenoid saponins, gummiferaosides A-C, showed cytotoxicity against the A2780 human ovarian cancer cell line with IC50 values of 0.8, 1.5, and 0.6 microg/mL, respectively. Expand
Elucidation of the pharmacophore of echinocystic acid, a new lead for blocking HCV entry.
To elucidate the pharmacophore of echinocystic acid (EA), an oleanane-type triterpene displaying substantial inhibitory activity on HCV entry, two microbial strains were utilized to modify the chemical structure of EA and it was demonstrated that ring A, B, C and the left side of ring E of EA are highly conserved, while ring D and the right side of rings E ofEA are flexible. Expand
Bioactive saponins from Acacia tenuifolia from the suriname rainforest.
Bioassay-guided fractionation of the MeOH extract of Acacia tenuifolia using the engineered yeast strains 1138, 1140, 1353, and Sc7 as the bioassay tool resulted in the isolation of the three newExpand