Carbon- 13 n.m.r. spectra of cardenolide glycosides. Configuration of the 11,12-epoxide in cerbertin

Journal of the Chemical Society, Perkin Transactions 1
1981.0

Abstract

The 13C n.m.r. data of the Digitalis and the Cerbera cardiac glycosides, and of ouabain and neriifolin, have been analysed. Both 13C and 1H n.m.r. results show that the 11,12-epoxide in cerbertin has an α-configuration. Here we present the 13C chemical-shift data of a number of natural cardenolides and their derivatives, viz. the Digitalis tri-β-D-digitoxosides digitoxin (1), digoxin (2), and 3'''-acetyldigoxin (3); the α-L-thevetosides neriifolin (6), cerbertin (8), 4'-acetylcerbertin (9), and deacetylcerbertin (7); and the α-L-rhamnoside ouabain (10). For comparison, data of the genins digitoxigenin (4) and digoxigenin (5) are also included.

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