Cardenolide analogues. 11. Improved method for the use of Fétizon's reagent in the synthesis of cardiac glycosides.
An improved procedure has been developed for preparing glycosides of cardenolide genins. The method uses specially prepared Fétizon's reagent as catalyst, combined, in most cases, with mercuric cyanide and mercuric bromide. In the presence of this catalyst, genins react readily, at room temperature, with per-acetylated 1-bromo-sugars to give the acetylated glycosides in high yield with little or no side reaction. The reaction proceeds almost to completion in 30 to 60 min. The free glycoside is obtained by mild deacetylation using triethylamine/methanol/water (20:20:1) at room temperature for 72 h. Proof of structure was obtained using chemical ionization mass spectrometry, NMR spectroscopy and comparison of physical constants with published data. The compounds were tested for inotropic activity using the isolated guinea pig atrium.
D000818:Animals; D002298:Cardenolides / Q000138:chemical synthesis* / Q000494:pharmacology; D002301:Cardiac Glycosides / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D006168:Guinea Pigs; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009200:Myocardial Contraction / Q000187:drug effects
D002298:Cardenolides; D002301:Cardiac Glycosides; D007202:Indicators and Reagents